Abstract:
The present invention provides a compound of the formula and pharmaceutically acceptable salts having useful antiviral activity against viruses of the herpes family.                            
     Wherein: 
     X=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 ; 
     Y=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8  or a chemical bond; 
     Z=NH, O, NR 8 , S, SO, SO 2 ; 
     The remaining substituents are described in the specification.

Description:
This application is a 371 of PCT/US00/32571 filed on Nov. 30, 2000 which claims benefit of Ser. No. 60/174,883 Jan. 7, 2000. 
    
    
     FIELD OF THE INVENTION 
     The present invention relates to compounds possessing antiviral activity against viruses of the herpes family, or a composition containing them. These compounds provide a method for treating herpes viral infections, including condition caused by herpes simplex I such as cold sores, herpes simplex II such as genital herpes, as well as shingles caused by herpes zoster and infections caused by cytomegalovirus, Epstein Barr Virus. 
     BACKGROUND OF INVENTION 
     Various subfamilies of herpes viruses (Herpes viridae) exist: α-herpesvirinae, β-herpesvirinae, γ-herpesvirinae and cercopithecing Herpes virus I (3 virus); some specific viruses are: Herpes simplex virus-I (HSV-1), Herpes simplex virus-2 HSV-2), Cytomegalovirus (CMV), Varicella Zoster virus (VZV), Epstein-Barr virus (EBV), human herpes virus-6 (HHV-6), human herpes virus-7 (HHV-7), human herpes virus-8 (HHV) as well as others which may not yet be defined. 
     The incidence of infections by Herpes simplex virus is very high throughout the world. Serological studies showed that herpes viral infections affect a substantial percentage of the population. Reactivation of herpes virus infections may lead to recurrent infections. The risk of severe diseases increases with decreasing immunocompetence of the host. There is a pressing need for improved therapy for treating this disease. Currently, exclusive of vaccines, treat involves primarily nucleoside drugs such as acyclovir, which target thymidine kinase and suffer from development of resistance. 
     SUMMARY OF THE INVENTION 
     The present invention provides a compound of the formula and its pharmaceutically acceptable salts, or the compound and its pharmaceutical composition having useful antiviral activity against viruses of the herpes family.                           
     wherein: 
     X=O, (CH 2 ) m , S, SO, SO 2 , NR 8  or a chemical bond; 
     Y=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 ; 
     Z=N, NH, O, NHR 8 , S, SO, SO 2 ; 
     n=an integer of from 0 to 2; 
     m=an integer of 1, 2, or 3; 
     R 1 , R 2 , R 3 , R 4 , R 5  independently are hydrogen, halogen, hydroxyl amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxy groups (1-6 carbon atoms), CF 3 , OCF 3 , aminoalkyl (1-6 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4 hetero atoms of N, O, or S; 
     Ar=phenyl, 
     substituted phenyl, 
     benzoheterocyclic ring, 
     substituted benzoheterocyclic ring, 
     heterocyclic ring, or 
     substituted heterocyclic ring, which have substitutions R 6  or R 7 ; 
     R 4  and R 7  are independently hydrogen, alkyl group (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), halogen, alkoxy, CF 3 , aminoalkyl (1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atoms with 1-4 heteroatoms of N, O or S; 
     R 6  and R 7  may also form a ring, optionally cycloalkyl or aryl or substituted aryl; R 8  is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above. 
     The invention also provides for a pharmaceutical composition for the treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises an amount of the compound of claim  1  sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier. 
     The invention also provides for a method of treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises administering to a subject in need of such treatment an effective antivirally dosage of a composition of formula I. 
    
    
     DESCRIPTION OF PREFERRED EMBODIMENTS 
     The present invention pertains to anti viral compounds. Preferred compounds are as follows: 
     One preferred compound is:                           
     Another preferred compound is:                           
     Another preferred compound is:                           
     Another preferred compound is:                           
     Another preferred compound is:                           
     Another preferred compound is:                           
     Another preferred compound is:                           
     The term “alkyl” means a straight or branched hydrocarbon radical having from 1 to 12 carbon atoms unless otherwise specified and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl n-nonyl, n-decyl, undecyl, and dodecyl. The alkyl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected from F, Cl, Br, I, OH, NH 2 , SH, CN, NO 2 , OCH 3 , OCH 2 CH 2 OH, NHCH 3 , or N(CH 3 ) 2 . 
     The term “cycloalkyl” means a hydrocarbon ring which contains from 3 to 12 carbon atoms unless otherwise specified, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Where possible, the cycloalkyl group may contain double bonds. The cycloalkyl ring may be unsubstituted or substituted by from 1 to 3 substituents selected from alkyl, cycloalkyl alkoxy, thioalkoxy all as defined herein, hydroxy, thiol, nitro, halogen, amino, formyl, carboxyl, nitrile, —NH—CO—R, —CO—NHR—, —CO 2 R, —COR, aryl, or heteroaryl wherein alkyl (R), aryl, and heteroaryl are defined as herein. 
     The term “alkoxy” having 1-6 carbon atoms means a C 1 -C 6  alkyl-O— group or radical wherein C 1 -C 6  alkyl has the meaning as defined above. Illustrative examples of a straight or branched alkoxy group or radical having from 1 to 6 carbon atoms, also known as a C 1 -C 6  alkoxy, include methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-butoxy, 2-methyl-1-propoxy, and 1,1-dimethylethoxy, 1-pentoxy, 2-pentoxy, 3-pentoxy, 2,2-dimethylpropoxy, 1-hexoxy, 2-hexoxy, 3-hexoxy, and 4-methyl-1-pentoxy. 
     The term “thioalkoxy” having 1-6 carbon atoms means a C 1 -C 6  alkyl-S— group or radical wherein C 1 -C 6  alkyl has the meaning as defined above. Illustrative examples of a straight or branched thioalkoxy group or radical having from 1 to 6 carbon atoms, also known as a C 1 -C 6  thioalkoxy, include methylthio, ethylthio, 1-propylthio, 2-propylthio, 1-butylthio and 2-butylthio, 1-pentylthio, 2-pentylthio, 3-pentylthio, 2,2-dimethylpropylthio, 1-hexylthio, 2-hexylthio, 3-hexylthio, and 4-methyl-1-pentylthio. 
     The term “aryl” means an aromatic carbocyclic ring having from 6 to 10 carbon atoms. Illustrative examples of an aryl group or radical include phenyl, 1-naphthyl, and 2-napthyl. The aryl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH 2 , SH, CN, NO 2 , OCH 3 , OCH 2 CH 2 OH, NHCH 3 , or N(CH 3 ) 2 . 
     The term “Oaryl” means an aryl-O— group or radical wherein aryl has the meaning as defined above. Illustrative examples of an Oaryl group or radical include phenoxy, 1-naphthyloxy, and 2-napthyloxy. Oaryl groups may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH 2 , SH, CN, NO 2 , OCH 3 , OCH 2 CH 2 OH, NHCH 3 , or N(CH 3 ) 2 . 
     The term “halogen” means bromine, chlorine, fluorine or iodine. 
     The term “monoalkylamino” means an NH-alkyl group or radical wherein alkyl has the meaning as defined above. 
     The term “dialkylamino” means an N-(alkyl) 2  group or radical wherein alkyl has the meaning as defined above. 
     The term “aminoalkyl” having 1-6 carbon atoms means an H 2 N—(C 1 -C 6  alkyl)-group or radical wherein C 1 -C 6  alkyl has the meaning as defined above. The aminoalkyl group is a substituted C 1 -C 6  alkyl group or radical containing at least one substituent which is NH 2 . 
     The term “aminoaryl” means an H 2 N-aryl-group or radical wherein aryl has the meaning as defined above. The aminoaryl group is a substituted aryl group or radical containing at least one substituent which is NH 2 . 
     The term “carbocycle” means cycloalkyl as defined above. 
     The term “heteroatom” means a nitrogen, sulfur, or oxygen. 
     The term “heterocycle” means a heterocyclic radical which are 5-7 atoms having 14 heteroatons and are selected from: furan, pyrrole, thiophene, oxazole, isoxazole, thiazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, piperazine, piperidine, morpholine, thiomorpholine, oxolane, dioxane, sulfolane, unsubstituted or substituted by 1 to 2 substituents selected from alkyl as defined above. For heterocycles containing sulfur, the oxidized sulfur heterocycles containing SO or SO 2  groups are also included. 
     The term “benzoheterocyclic ring” (“fused heterocycle”) refers to a heterocycle that is adjoined at two consecutive positions with a phenyl ring or another heterocycle, such rings may include 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolinyl, 2-, 3-, 4-, 5-, 6-, or 7-indolyl, 2-, 3-, 4-, 5-, 6-, or 7-benzo[b]thienyl, 2-, 4-, 5-, 6-, or 7-benzoxazolyl, 2-, 4-, 5-, 6-, or 7-benzimidazolyl, 2-, 4-, 5-, 6-, or 7-benzothiazolyl. 
     Some of the compounds of Formula I are capable of further forming pharmaceutically acceptable acid-addition and/or base salts. All of these forms are within the scope of the present invention. 
     Pharmaceutically acceptable acid addition salts of the compounds of Formula I include salts derived from nontoxic inorganic acids such as hydrochloric, nitric, phosphoric, sulfuric, hydrobromic, hydriodic, hydrofluoric, phosphorous, and the like, as well as the salts derived from nontoxic organic acids, such as aliphatic mono- and dicarboxylic acids, phenyl-substituted alkanoic acids, hydroxy alkanoic acids, alkanedioic acids, aromatic acids, aliphatic and aromatic sulfonic acids, etc. Such salt thus include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihyrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, acetate, trifluoroacetate, propionate, caprylate, isobutyrate, oxalate, malonate, succinates suberate, sebacate, fumarate, maleate, mandelate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, phthalate, benzenesulfonate, toluenesulfonate, phenylacetate, citrate, lactate, maleate, tartrate, methanesulfonate, and the like. Also contemplated are salts of amino acids such as arginate and the like and gluconate, galacturonate (see, for example, Berge S. M., et al., “Pharmaceutical Salts,”  Journal of Pharmaceutical Science , 1977;66: 1-19. 
     The acid addition salt of said basic compounds are prepared by contacting the free base form with a sufficient amount of the desired acid to produce the salt in the conventional manner. 
     Pharmaceutically acceptable base addition salts are formed with metals or amines, such as alkali and alkaline earth metals or organic amines. Examples of metals used as cations are sodium, potassium, magnesium, calcium, and the like. Examples of suitable amines are N,N′-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, dicyclohexylamine, ethylenediamine, N-methylglucamine, and procaine (see, for example, Berge, supra., 1977). 
     The base addition salts of said acidic compounds are prepared by contacting the free acid form with a sufficient amount of the desired base to produce the salt in the conventional manner. 
     Certain of the compounds of the present invention can exist in unsolvated forms as well as solvated forms, including hydrated forms. In general, the solvated forms, including hydrated forms, are equivalent to unsolvated forms and are intended to be encompassed within the scope of the present invention. 
     Certain of the compounds of the present invention possess one or more chiral centers and each center may exist in the R(D) or S(L) configuration. The present invention includes all enantiomeric and epimeric forms as well as the appropriate mixtures thereof. Configuration drawn is most preferred. 
     The compounds of the present invention can be prepared and administered in a wide variety of oral and parenteral dosage forms. Thus, the compounds of the present invention can be administered by injection, that is, intravenously, intramuscularly, intracutaneously, subcutaneously, intraduodenally, or intraperitoneally. Also, the compounds of the present invention can be administered by inhalation, for example, intranasally. Additionally, the compounds of the present invention can be administered transdermally. It will be obvious to those skilled in the art that the following dosage forms may comprise as the active component, either a compound of Formula I or a corresponding pharmaceutically acceptable salt of a compound of Formula I. 
     For preparing pharmaceutical compositions from the compounds of the present invention, pharmaceutically acceptable carriers can be either solid or liquid. Solid form preparations include powders, tablets, pills, capsules, cachets, suppositories, and dispersible granules. A solid carrier can be one or more substances, which may also act as diluents, flavoring agents, binders, preservatives, tablet disintegrating agents, or an encapsulating material. 
     In powders, the carrier is a finely divided solid, which is in a mixture with the finely divided active component. 
     In tablets, the active component is mixed with the carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired. 
     The powders and tablets preferably contain from five or ten to about seventy percent of the active compound. Suitable carriers are magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, dextrin, starch, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose, a low melting wax, cocoa butter, and the like. The term “preparation” is intended to include the formulation of the active compound with encapsulating material as a carrier providing a capsule in which the active component with or without other carriers, is surrounded by a carrier, which is thus in association with it. Similarly, cachets and lozenges are included. Tablets, powders, capsules, pills, cachets, and lozenges can be used as solid dosage forms suitable for oral administration. 
     For preparing suppositories, a low melting wax, such as a mixture of fatty acid glycerides or cocoa butter, is first melted, and the active component is dispersed homogeneously therein, as by stirring. The molten homogenous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify. 
     Liquid form preparations include solutions, suspensions, and emulsions, for example, water or water propylene glycol solutions. For parenteral injection, liquid preparations can be formulated in solution in aqueous polyethylene glycol solution. 
     Aqueous solutions suitable for oral use can be prepared by dissolving the active component in water and adding suitable colorants, flavors, stabilizing and thickening agents as desired. 
     Aqueous suspensions suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, such as natural or, synthetic gums, resins, methylcellulose, sodium carboxymethylcellulose, and other well-known suspending agents. 
     Also included are solid form preparations, which are intended to be converted, shortly before use, to liquid form preparations for oral administration. Such liquid forms include solutions, suspensions, and emulsions. These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thickeners, solubilizing agents, and the like. 
     The pharmaceutical preparation is preferably in unit dosage form. In such form the preparation is divided into unit doses containing appropriate quantities of the active component. The unit dosage form can be a packaged preparation, the package containing discrete quantities of preparation, such as packeted tablets, capsules, and powders in vials or ampoules. Also, the unit dosage form can be a capsule, tablet, cachet, or lozenge itself or it can be the appropriate number of any of these in packaged form. 
     The quantity of active component in a unit dose preparation may be varied or adjusted from 0.1 mg to 100 mg preferably 0.5 mg to 100 mg according to the particular application and the potency of the active component. The composition can, if desired, also contain other compatible therapeutic agents. 
     In therapeutic use as antagonists of a virus, as agents for the treatment of infections caused by a virus or as agents for the treatment of diseases due to a virus, the compounds utilized in the pharmaceutical method of this invention are administered at the initial dosage of about 0.01 mg to about 100 mg/kg daily. A daily dose range of about 0.01-mg to about 10 mg/kg is preferred. The dosages, however, may be varied depending upon the requirements of the patient, the severity of the condition being treated, the compound being employed. Determination of the proper dosage for a particular situation is within the skill of the art. Generally, treatment is initiated with smaller dosages, which are less than the optimum dose of the compound. Thereafter, the dosage is increased by small increments until the optimum effect under the circumstances is reached. For convenience, the total daily dosage may be divided and administered in portions during the day, if desired. 
     General Procedure 1 (for Singleton Synthesis) 
     Reductive Amination of Aryl Amines with Aldehydes or Ketones. 
     Reagent 2 (1 eq.) was taken in a solvent (dichloromethane, 1,2-dichloroethane or tetrahydrofuran or diethyl ether) and to it reagent 1 (1 to 1.2 eq.) was added. To this solution cooled at 0° C. was added a reducing agent (sodium cyanoborohydride or sodium triacetoxyborohydride) (1 to 2 eq.). To it a drop of acetic acid was added and kept under stirring at room temperature for 6 to 24 hours. The excess hydride was quenched by adding methanol. The reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution, aqueous sodium bisulfite and brine; dried over anhydrous magnesium sulfuate or sodium sulphate. Organic layer was concentrated and crude product was purified by flash silica gel chromatography to afford the final product. The products were characterized by spectral data. The compounds synthesized using this procedure are shown in Table 4. 
     General Procedure 2 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis) 
     
       
                 
         
             
             
         
      
     
     To a 2-dram glass vial were added, by Tecan liquid handling robot, a solution of reagent 2 (0.05 mmol) in trimethyl orthoformate (0.2 ml) followed by reagent 1 (0.05 mmol) in trimethyl orthoformate (0.2 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan™ liquid handling robot, 1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23mg) was added manually to each vial. A solution of acetic acid (0.05 mmol) in dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (1 ml). The reaction nature was then transferred, by Tecan liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 M disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromotography mass spec). 
     General Procedure 3 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis) 
     
       
                 
         
             
             
         
      
     
     To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in N,N-di-methylformamide (0.1 ml) followed by reagent 1 (0.05 mmol) in N,N-dimethylformnamide (0.1 ml). Each vial was treated with trimethylorthoformate (0.2 ml) by Tecan™ liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan™ liquid handling robot 1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23mg) was added manually to each vial. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot The vial was again capped and the reaction mixture was shaken at room temperate for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec). 
     General Procedure 4 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis) 
     
       
                 
         
             
             
         
      
     
     To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followed by reagent 1 (0.2 mmol) in methanol (0.2 ml). To each vial was added, by Tecan™ liquid handling robot, a 1N solution of sodium cyanoborohydride in methanol (0.2 ml) and a 10% a acetic acid in methanol (0.05 ml) solution. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec). 
     General Procedure 5 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis) 
     
       
                 
         
             
             
         
      
     
     To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in 1,2-dichloroethane (0.2 ml) followed by reagent 1 (0.15 mmol) in 1,2-dichloroethane (0.1 ml). To each vial solid sodium triacetoxyborohydride (˜25 mg) was added manually. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec). 
     General Procedure 6 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis) 
     
       
                 
         
             
             
         
      
     
     To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followed by reagent 1 (0.15 mmol) in methanol (0.1 ml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanol solution (0.05 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec). 
     General Procedure 7 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis) 
     
       
                 
         
             
             
         
      
     
     To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) followed by reagent 1 in N,N-dimethylformamide (0.32 ml) or methanol (0.2 ml). The vials were then concentrated overnight to dryness. Each vial was treated by Tecan™ liquid handling robot with reagent 1 (0.15 mmol) in methanol (0.1 ml) and methanol (0.2 ml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanol solution (0.05 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec). 
     Synthesis of Compound 450: To dibenzofuran-2-yl-amine (0.91 g, 5 mmol) taken in dichloromethane (75 mL) was added α,α′-dibromo-ortho-xylene (1.85 g, 7 mmol) followed by triethylamine (3.03 g, 30 mmol. The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (1.43 g). 
     Synthesis of Compound 451: To dibenzofuran-2-yl-amine (0.91 g, 5 mmol) taken in dichloromethane (75 mL) was added phthaloyl dichloride (1.16 g, 6 mmol) followed by triethylamine (3.03 g, 30 mmol). The reaction was stirred at room temperature for 5 minutes. The reaction was quenched with sodium bicarbonate solution and the organic layer was separated. The crude product was purified by flash silica gel chromatography to give the title compound (0.51 g). 
     Synthesis of Compound 463: To compound 58 (0.25 g, 0.87 mmol) taken in tetrahydrofuran (10 mL) was added sodium hydride (60% in mineral oil, 0.035 g, 0.87 mmol). To it methyl iodide (0.25 g, 1.74 mmol was added. The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (0.18 g). 
     Deprotection of t-butyloxycarbonyl group: The general procedure for the removal of tert-butyoxycarbonyl (Boc) group is as follows: To the compound taken a flask was added hydrochloric acid in an appropriate solvent (dioxane, methanol, 1,2-dichloromethane and the reaction was kept under shaking for 5 to 18 hours. Removal of volatiles furnished the corresponding product. 
     Reagents 1 are shown in Table 1. 
     
       
         
               
             
               
               
             
               
               
             
           
               
                 TABLE 1 
               
             
             
               
                   
               
               
                 Aldehydes/ketones (reagent 1) 
               
             
          
           
               
                 No. 
                 Reagent 1 (aldehydes/ketones) 
               
               
                   
               
             
          
           
               
                 1 
                 o-tolualdehyde 
               
               
                 2 
                 meta-tolualdehyde 
               
               
                 3 
                 para-tolualdehyde 
               
               
                 4 
                 2-fluorobenzaldehyde 
               
               
                 5 
                 3-fluorobenzaldehyde 
               
               
                 6 
                 4-fluorobenzaldehyde 
               
               
                 7 
                 4-tert-butylbenzaldehyde 
               
               
                 8 
                 α,α,α-Trilfluoro-o-tolualdehyde 
               
               
                 9 
                 α,α,α-Trilfluoro-m-tolualdehyde 
               
               
                 10 
                 α,α,α-Trilfluoro-p-tolualdehyde 
               
               
                 11 
                 o-anisaldehyde 
               
               
                 12 
                 m-anisaldehyde 
               
               
                 13 
                 p-anisaldehyde 
               
               
                 14 
                 Salicylaldehyde 
               
               
                 15 
                 3-hydroxybenzaldehyde 
               
               
                 16 
                 4-hydroxybenzaldehyde 
               
               
                 17 
                 2-chlorobenzaldehyde 
               
               
                 18 
                 3-chlorobenzaldehyde 
               
               
                 19 
                 4-chlorobenzaldehyde 
               
               
                 20 
                 3-benzyloxybenzaldehyde 
               
               
                 21 
                 4-benzyloxybenzaldehyde 
               
               
                 22 
                 2,3-dimethoxybenzaldehyde 
               
               
                 23 
                 2,4-dimethoxybenzaldehyde 
               
               
                 24 
                 2,5-dimethoxybenzaldehyde 
               
               
                 25 
                 2,6-dimethoxybenzaldehyde 
               
               
                 26 
                 3,4-dimethoxybenzaldehyde 
               
               
                 27 
                 3,5-dimethoxybenzaldehyde 
               
               
                 28 
                 1,4-Benzodioxan-6-carboxaldehyde 
               
               
                 29 
                 2,4-dimethylbenzaldehyde 
               
               
                 30 
                 2,5-dimethylbenzaldehyde 
               
               
                 31 
                 2,3-difluorobenzaldehyde 
               
               
                 32 
                 2,4-difluorobenzaldehyde 
               
               
                 33 
                 2,5-difluorobenzaldehyde 
               
               
                 34 
                 2,6-difluorobenzaldehyde 
               
               
                 35 
                 3,4-difluorobenzaldehyde 
               
               
                 35 
                 3,5-difluorobenzaldehyde 
               
               
                 37 
                 2,3,4-trifluorobenzaldehyde 
               
               
                 38 
                 2,3,6-trifluorobenzaldehyde 
               
               
                 39 
                 3-fluoro-2-methylbenzaldehyde 
               
               
                 40 
                 3-fluoro-p-anisaldehyde 
               
               
                 41 
                 2-pyridinecarboxaldehyde 
               
               
                 42 
                 3-pyridinecarboxaldehyde 
               
               
                 43 
                 4-pyridinecarboxaldehyde 
               
               
                 44 
                 4-pyridinecarboxaldehyde N-oxide 
               
               
                 45 
                 6-methyl-2-pyridinecarboxaldehyde 
               
               
                 46 
                 3-furaldehyde 
               
               
                 47 
                 2-furaldehyde 
               
               
                 48 
                 5-chloro-2-thiophenecarboxaldehyde 
               
               
                 49 
                 3-thiophenecarboxaldehyde 
               
               
                 50 
                 2-thiophenecarboxaldehyde 
               
               
                 51 
                 pyrrole-2-carboxaldehyde 
               
               
                 52 
                 1-methyl-2-pyrrolecarboxaldehyde 
               
               
                 53 
                 1-naphthaldehyde 
               
               
                 54 
                 2-naphthaldehyde 
               
               
                 55 
                 2-quinolinecarboxaldehyde 
               
               
                 56 
                 3-quinolinecarboxaldehyde 
               
               
                 57 
                 4-quinolinecarboxaldehyde 
               
               
                 58 
                 indole-3-carboxaldehyde 
               
               
                 59 
                 2-bromobenzaldehyde 
               
               
                 60 
                 2-chlorobenzaldehyde 
               
               
                 61 
                 2-ethoxybenzaldehyde 
               
               
                 62 
                 2-cyanobenzaldehyde 
               
               
                 63 
                 5-(2-chlorophenyl)furfural 
               
               
                 64 
                 5-(3-chlorophenyl)furfural 
               
               
                 65 
                 5-(4-chlorophenyl)furfural 
               
               
                 66 
                 2-thiazolecarboxaldehyde 
               
               
                 67 
                 2-imidazolecarboxaldehyde 
               
               
                 68 
                 4(5)-imidazolecaboxaldehyde 
               
               
                 69 
                 5-nitro-2-thiophenecarboxaldehyde 
               
               
                 70 
                 2-nitrobenzaldehyde 
               
               
                 71 
                 4-formyluracil 
               
               
                 72 
                 4-acetoxybenzaldehyde 
               
               
                 73 
                 4-(dimethylamino)benzaldehyde 
               
               
                 74 
                 1-acetyl-3-indolecarboxaldehyde 
               
               
                 75 
                 4-bromo-2-thiophenecarboxaldehyde 
               
               
                 76 
                 Piperonal 
               
               
                 77 
                 3-trifluoromethoxybenzaldehyde 
               
               
                 78 
                 4-chloro-3-nitro-benzaldehyde 
               
               
                 79 
                 Benzaldehyde 
               
               
                 80 
                 3-benzyloxybenzaldehyde 
               
               
                 81 
                 3-phenoxybenzaldehyde 
               
               
                 82 
                 2-butanone 
               
               
                 83 
                 2-Pentanone 
               
               
                 84 
                 3-Methyl-2-butanone 
               
               
                 85 
                 Tetrahydrothiophene-3-one 
               
               
                 86 
                 Tetrahydrothiopyran-4-one 
               
               
                 87 
                 Cycloheptanone 
               
               
                 88 
                 Cyclooctanone 
               
               
                 89 
                 Cyclohexylmethylketone 
               
               
                 90 
                 4-Methyl-2-pentanone 
               
               
                 91 
                 3-Pentanone 
               
               
                 92 
                 3-Hexanone 
               
               
                 93 
                 4-Hydroxy-3-methyl-2-butanon 
               
               
                 94 
                 2-Methoxyphenylacetone 
               
               
                 95 
                 4-nitrobenzaldehyde 
               
               
                 96 
                 4-(methylthio)benzaldehyde 
               
               
                 97 
                 Propionaldehyde 
               
               
                 98 
                 Isovaleraldehyde 
               
               
                 99 
                 3-(methylthio)propionaklehyde 
               
               
                 100 
                 1-phenyl-2-pentanone 
               
               
                 101 
                 Acetone 
               
               
                 102 
                 Cyclopropyl methyl ketone 
               
               
                 103 
                 Cyclohexanone 
               
               
                 104 
                 n-tert-butoxycarbonyl-4-piperidone 
               
               
                 105 
                 3,3,5,5-tetramethylcyclohexanone 
               
               
                 106 
                 1-decalone 
               
               
                 107 
                 4-cyclohexylcyclohexanone 
               
               
                 108 
                 2-norbornanone 
               
               
                 109 
                 4-tert-butylcyclohexanone 
               
               
                 110 
                 Cyclopentanone 
               
               
                 111 
                 2-adamantanone 
               
               
                 112 
                 Bicyclo[3,2,1]octan-2-one 
               
               
                 113 
                 1,1-dioxo-tetrahydro-thiopyran-4-one 
               
               
                   
               
             
          
         
       
     
     Reagent 2 (amines) used in the above general procedures are shown in Table 2: 
     
       
         
               
               
             
               
               
             
           
               
                         TABLE 2 
               
               
                   
               
               
                 No. 
                 Reagent 2 (amines) 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 1 
                 Dibenzofuran-2-yl-methyl-amine 
               
               
                 2 
                 8-fluoro-dibenzofuran-2-yl-amine 
               
               
                 3 
                 8-chloro-dibenzofuran-2-yl-amine 
               
               
                 4 
                 8-amino-dibenzofuran-2-ol 
               
               
                 5 
                 3-methoxy-diebenzofuran-2-yl-amine 
               
               
                 6 
                 9H-Fluoren-3-yl-amine 
               
               
                 7 
                 9H-Fluorene-2-yl-amine 
               
               
                 8 
                 Dibenzofuran-4-yl-amine 
               
               
                 9 
                 Benzo[4,5]furo[2,3-H]pyridin-3-yl-amine 
               
               
                 10 
                 9-Ethyl-9H-carbazol-3-ylamine 
               
               
                 11 
                 3-Amino-carbazole-9-carboxylic acid tert-butyl ester 
               
               
                 12 
                 Dibenzofuran-2-yl-methyl-amine 
               
               
                 13 
                 Dibenzofuran-2-yl-dimethyl-amine 
               
               
                 14 
                 Dibenzothiophene-2-yl-amine 
               
               
                 15 
                 Dibenzothiophene-3-yl-amine 
               
               
                 16 
                 6-Amino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid 
               
               
                   
                 tert-butyl ester 
               
               
                 17 
                 Dibenzo[1,4]dioxin-2-yl-amine 
               
               
                 18 
                 Phenoxanthiin-3-yl-amine 
               
               
                 19 
                 10-Oxa-9-thia-1-aza-anthracen-3-yl-amine 
               
               
                 20 
                 10H-Benzo-b]pyrido[2,3-e][1,4]oxazin-3-ylamine acetic acid, 
               
               
                   
                 tert-butyl ester 
               
               
                 21 
                 Anthracen-2-yl-amine 
               
               
                 22 
                 10,111-Dihydro-5H-diebnzo[b,f]azepin-3-yl-amine 
               
               
                 23 
                 6,7,8,9-Tetrahydro-5H-carbazol-3-yl-amine 
               
               
                 24 
                 7-Amino-1-aza-phenoxathiin 
               
               
                   
               
             
          
         
       
     
     The compounds of Formula I include: 
     
       
         
               
               
             
           
               
                   
               
             
             
               
                 1 
                 (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 2 
                 Cyclopentyl-(9H-fluoren-2-yl)-amine 
               
               
                 3 
                 (1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine 
               
               
                 4 
                 N 3 -Cyclopentyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 5 
                 Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 6 
                 (2-Methoxy-dibenzofuran-3-yl)-(terahydro-thiopyran-4-yl)-amine 
               
               
                 7 
                 Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 8 
                 (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 9 
                 sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 10 
                 N 2 ,N 2 -Dimethyl-N 3 -piperidin-4-yl-9H-fluorene-2,3-diamine 
               
               
                 11 
                 N 3 -(1-Benzyl-butyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 12 
                 (9H-Fluoren-2-yl)-piperidin-4-yl-amine 
               
               
                 13 
                 (1-Benzyl-butyl)-(9H-fluoren-2-yl-amine 
               
               
                 14 
                 sec-Butyl-(9H-fluoren-2-yl)-amine 
               
               
                 15 
                 (1,1-Diox-hexahydro-thiopyran-4-yl)-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 16 
                 Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-amine 
               
               
                 17 
                 (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine 
               
               
                 18 
                 Adamantan-2-yl-dibenzofuran-2-yl-amine 
               
               
                 19 
                 Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine 
               
               
                 20 
                 Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine 
               
               
                 21 
                 (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine 
               
               
                 22 
                 Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine 
               
               
                 23 
                 Cyclopentyl-dibenzofuran-2-yl-amine 
               
               
                 24 
                 Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine 
               
               
                 25 
                 Cyclohexyl-(9H-fluoren-2-yl)-amine 
               
               
                 26 
                 Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine 
               
               
                 27 
                 Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine 
               
               
                 28 
                 Dibenzofuran-2-yl-dipropyl-amine 
               
               
                 29 
                 N 3 -(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3- 
               
               
                   
                 diamine 
               
               
                 30 
                 N 3 -Isopropyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 31 
                 N 2 ,N 2 -Dimethyl-N 3 -(tetrahydro-thiopyran-4-yl)-9H-fluorene-2,3-diamine 
               
               
                 32 
                 N 3 -Cyclohexyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 33 
                 N 3 -Cyclohexyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 34 
                 N 3 -(1-Ethyl-propyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 35 
                 N 3 -(1-Cyclopropyl-ethyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 36 
                 N 3 -sec-Butyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine 
               
               
                 37 
                 (9H-Fluoren-2-yl)-isopropyl-amine 
               
               
                 38 
                 (9H-Fluoren-2-yl)-(tetahydro-thiopyran-4-yl)-amine 
               
               
                 39 
                 Cycloheptyl-(9H-fluoren-2-yl)-amine 
               
               
                 40 
                 Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine 
               
               
                 41 
                 Dibenzofuran-2-yl-piperidin-4-yl-amine 
               
               
                 42 
                 Dibenzofuran 2-yl-isopropyl-amine 
               
               
                 43 
                 Cyclohexyl-dibenzofuran-2-yl-amine 
               
               
                 44 
                 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine 
               
               
                 45 
                 Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine 
               
               
                 46 
                 Dibenzofuran-3-yl-piperidin-4-yl-amine 
               
               
                 47 
                 Dibenzofuran-3-yl-isopropyl-amine 
               
               
                 48 
                 Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine 
               
               
                 49 
                 Cyclohexyl-dibenzofuran-3-yl-amine 
               
               
                 50 
                 Cycloheptyl-dibenzofuran-3-yl-amine 
               
               
                 51 
                 (4-Chloro-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 52 
                 (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 53 
                 Dibenzofuran-2-yl-(3-trifluoromethyoxy-benzyl)-amine 
               
               
                 54 
                 Benzo[1,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine 
               
               
                 55 
                 Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine 
               
               
                 56 
                 Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine 
               
               
                 57 
                 Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine 
               
               
                 58 
                 Dibenzofuran-2-yl-(2-methyl-benzyl)-amine 
               
               
                 59 
                 Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine 
               
               
                 60 
                 Dibenzofuran-2-yl-(4-nitro-benzyl)-amine 
               
               
                 61 
                 Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine 
               
               
                 62 
                 Dibenzofuran-2-yl-(4-methyl-benzyl)-amine 
               
               
                 63 
                 Benzyl-dibenzofuran-2-yl-amine 
               
               
                 64 
                 (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 65 
                 (1-Benzyl-butyl)-dibenzofuran-2-yl-amine 
               
               
                 66 
                 Dibenzofuran-2-yl-8 2-(2-methoxy-phenyl)-1-methyl-ethyl]-amine 
               
               
                 67 
                 3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol 
               
               
                 68 
                 Dibenzofuran-2-yl-(1-ethyl-butyl)-amine 
               
               
                 69 
                 Dibenzofuran-2-yl-(1-ethyl-propyl)-amine 
               
               
                 70 
                 Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine 
               
               
                 71 
                 (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine 
               
               
                 72 
                 Cyclooctyl-dibenzofuran-2-yl-amine 
               
               
                 73 
                 Cycloheptyl-dibenzofuran-2-yl-amine 
               
               
                 74 
                 Dibenzofuran-2-yl-(tetrahydro-thiopyran-4-yl)-amine 
               
               
                 75 
                 Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine 
               
               
                 76 
                 Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine 
               
               
                 77 
                 Dibenzofuran-2-yl-(1-methyl-butyl)-amine 
               
               
                 78 
                 sec-Butyl-dibenzofuran-2-yl-amine 
               
               
                 79 
                 Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine 
               
               
                 80 
                 Benzofuro[3,3-b]pyridin-8-yl-pyridin-4-ylmethyl-amine 
               
               
                 81 
                 Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine 
               
               
                 82 
                 N-(2-Fluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 83 
                 N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-diamine 
               
               
                 84 
                 N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-2,8-diamine 
               
               
                 85 
                 N-(4-Methanesulfonyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 86 
                 N-Methyl-N′-pyridin-4-ylmethyl-dibensofuran-2,8-diamine 
               
               
                 87 
                 N-Methyl-N′-(2-methyl-benzyl)-dibenzofuran-2,8-diamine 
               
               
                 88 
                 Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine 
               
               
                 89 
                 (4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 90 
                 (3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 
               
               
                 91 
                 (2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 
               
               
                 92 
                 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-ylmethyl-amine 
               
               
                 93 
                 Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 
               
               
                 94 
                 (4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 
               
               
                 95 
                 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-ylmethyl-amine 
               
               
                 96 
                 (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-4-yl)-amine 
               
               
                 97 
                 Anthracen-2-yl-quinolin-4-ylmethyl-amine 
               
               
                 98 
                 Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine 
               
               
                 99 
                 Anthracen-2-yl-pyridin-4-ylmethyl-amine 
               
               
                 100 
                 Anthracen-2-yl-(2-methyl-benzyl)-amine 
               
               
                 101 
                 Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine 
               
               
                 102 
                 Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine 
               
               
                 103 
                 Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine 
               
               
                 104 
                 Dibenzo[b,e][1,4]fioxin 2-yl-naphthalen-1-ylmethyl-amine 
               
               
                 105 
                 Dibenzo[b,e][1,4]fioxin 2-yl-(4-methanesulfonyl-benzyl)-amine 
               
               
                 106 
                 Dibenzo[b,e][1,4]fioxin 2-yl-pyridin-4-ylmethyl-amine 
               
               
                 107 
                 8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol 
               
               
                 108 
                 8-(2-Fluoro-benzylamino)-dibenzofuran2-ol 
               
               
                 109 
                 8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol 
               
               
                 110 
                 8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol 
               
               
                 111 
                 8-(2-Methyl-benzylamino)-dibenzofuran-2-ol 
               
               
                 112 
                 (8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine 
               
               
                 113 
                 8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 
               
               
                 114 
                 8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine 
               
               
                 115 
                 (4-methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine 
               
               
                 116 
                 Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-SH-carbazol-3-yl)-amine 
               
               
                 117 
                 Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 118 
                 Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine 
               
               
                 119 
                 Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine 
               
               
                 120 
                 (4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 121 
                 Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine 
               
               
                 122 
                 Dibenzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine 
               
               
                 123 
                 Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine 
               
               
                 124 
                 Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 125 
                 N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 126 
                 N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 127 
                 N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 128 
                 N-Benzyl-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 129 
                 2-[(8-Methylamino-dibenzofuran-2-ylamino)-methyl]-benzonitrile 
               
               
                 130 
                 (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 131 
                 (8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 
               
               
                 132 
                 (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 133 
                 (3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 134 
                 (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 135 
                 (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 136 
                 Benzyl-phenoxathiin-3-yl-amine 
               
               
                 137 
                 (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 138 
                 (8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)-amine 
               
               
                 139 
                 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 140 
                 Benzyl-(8-chloro-dibenzofuran-2-yl)-amine 
               
               
                 141 
                 (9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine 
               
               
                 142 
                 (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine 
               
               
                 143 
                 (9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine 
               
               
                 144 
                 (3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 145 
                 (9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 146 
                 (4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 147 
                 Benzyl-(9H-fluoren-2-yl)-amine 
               
               
                 148 
                 (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine 
               
               
                 149 
                 (2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine 
               
               
                 150 
                 Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine 
               
               
                 151 
                 2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 
               
               
                 152 
                 Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine 
               
               
                 153 
                 Dibenzofuran-4-yl-(3,5-dimethoxy-benzyl)-amine 
               
               
                 154 
                 Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 155 
                 (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine 
               
               
                 156 
                 Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine 
               
               
                 157 
                 N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 158 
                 (8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine 
               
               
                 159 
                 (8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine 
               
               
                 160 
                 Dibenzofuran-4-yl-(2,4-dimethyl-benzyl)-amine 
               
               
                 161 
                 N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-diamine 
               
               
                 162 
                 N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-diamine 
               
               
                 163 
                 (2-Bromo-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 164 
                 Phenoxathiin-3-yl-quiolin-4-ylmethyl-amine 
               
               
                 165 
                 Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine 
               
               
                 166 
                 (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine 
               
               
                 167 
                 Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine 
               
               
                 168 
                 Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine 
               
               
                 169 
                 (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 
               
               
                 170 
                 (2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 171 
                 (8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine 
               
               
                 172 
                 (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine 
               
               
                 173 
                 (5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbozol-3-yl)-amine 
               
               
                 174 
                 (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine 
               
               
                 175 
                 (2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 176 
                 (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 
               
               
                 177 
                 (9H-Fluoren 2-yl)-quinolin-2-ylmethyl-amine 
               
               
                 178 
                 (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine 
               
               
                 179 
                 (9H-Fluoren-2-yl)-(3-methyl-pyridin-2 ylmethyl)-amine 
               
               
                 180 
                 (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine 
               
               
                 181 
                 (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine 
               
               
                 182 
                 (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine 
               
               
                 183 
                 (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 
               
               
                 184 
                 Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine 
               
               
                 185 
                 Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine 
               
               
                 186 
                 Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine 
               
               
                 187 
                 Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine 
               
               
                 188 
                 Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine 
               
               
                 189 
                 Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine 
               
               
                 190 
                 Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine 
               
               
                 191 
                 (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine 
               
               
                 192 
                 (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 
               
               
                 193 
                 N-Methyl-N′-(2,3,6-trifluro-benzyl)-dibenzofuran-2,8-diamine 
               
               
                 194 
                 N-Methyl-N′-(2,3,4-trifluro-benzyl)-dibenzofuran-2,8-diamine 
               
               
                 195 
                 N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 196 
                 N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 197 
                 N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 198 
                 N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 199 
                 N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 200 
                 N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 201 
                 N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-N′-methyl-dibenzofuran-2,8- 
               
               
                   
                 diamne 
               
               
                 202 
                 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 203 
                 (8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 204 
                 Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 205 
                 Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 206 
                 (2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 207 
                 (2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 208 
                 (2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 209 
                 (2,3-Difluoro-benzyl)-phenoxathiin-3-yl amine 
               
               
                 210 
                 (2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 211 
                 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenoxathiin-3-yl-amine 
               
               
                 212 
                 Benzo[b]thiophen 5-yl-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 213 
                 (8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 214 
                 (8-Chloro-dibenzofuran-2 yl)-(2,6-difluoro-benzyl)-amine 
               
               
                 215 
                 (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-amine 
               
               
                 216 
                 (8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)-amine 
               
               
                 217 
                 (9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 218 
                 (8-Chloro-dibenzofiram-2-yl)-(2,3-difluoro-benzyl)-amine 
               
               
                 219 
                 (9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 220 
                 (9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 221 
                 (2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 222 
                 (2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 223 
                 (2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 224 
                 (2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 225 
                 (2,5-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 226 
                 (2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 227 
                 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine 
               
               
                 228 
                 (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl-amine 
               
               
                 229 
                 (8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)-amine 
               
               
                 230 
                 (9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 231 
                 (9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 232 
                 (2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 233 
                 (2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 234 
                 (2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 235 
                 (2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 236 
                 (2,4-Dimethyl-benzyl)-(9H-fluoren-2 yl)-amine 
               
               
                 237 
                 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluroen-2-yl)-amine 
               
               
                 238 
                 (8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)-amine 
               
               
                 239 
                 Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine 
               
               
                 240 
                 Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 241 
                 N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 
               
               
                 242 
                 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 243 
                 (8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine 
               
               
                 244 
                 (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 245 
                 (2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 246 
                 (2-Chloro-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 247 
                 (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 248 
                 (2-Methyl-benzyl)-phenoxathiin-3-yl-amine 
               
               
                 249 
                 Anthracen-2-yl-(2-chloro-benzyl)-amine 
               
               
                 250 
                 Anthracen-2-yl-(2-fluoro-benzyl)-amine 
               
               
                 251 
                 Dibenzo[1,4]dioxin-2-yl-(2,3-dimethyoxy-benzyl)-amine 
               
               
                 252 
                 (2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine 
               
               
                 253 
                 2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol 
               
               
                 254 
                 Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine 
               
               
                 255 
                 2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol 
               
               
                 256 
                 (9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine 
               
               
                 257 
                 (9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine 
               
               
                 258 
                 (2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine 
               
               
                 259 
                 2-[(9H-Fluoren-2-ylamino)-methyl]-phenol 
               
               
                 260 
                 (9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine 
               
               
                 261 
                 (9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine 
               
               
                 262 
                 (9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine 
               
               
                 263 
                 Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine 
               
               
                 264 
                 Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine 
               
               
                 265 
                 2-(Dibenzofuran-4-ylaminomethyl)-phenol 
               
               
                 266 
                 Dibenzofuran-4-yl-(2-methoxy-benzyl)-amine 
               
               
                 267 
                 (2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 
               
               
                 268 
                 (2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 
               
               
                 269 
                 (2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 
               
               
                 270 
                 Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine 
               
               
                 271 
                 Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine 
               
               
                 272 
                 (2-Bromo-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 273 
                 (8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)-amine 
               
               
                 274 
                 2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 
               
               
                 275 
                 (2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 276 
                 (8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)-amine 
               
               
                 277 
                 (2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 278 
                 (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine 
               
               
                 279 
                 (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine 
               
               
                 280 
                 Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine 
               
               
                 281 
                 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-amine 
               
               
                 282 
                 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 
               
               
                 283 
                 Dibenzofuran-2-yl-(2-nitro-benzyl)-amine 
               
               
                 284 
                 Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine 
               
               
                 285 
                 2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile 
               
               
                 286 
                 Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine 
               
               
                 287 
                 Dibenzofuran-2-yl-(3-trifluoromethyl-benzyl)-amine 
               
               
                 288 
                 (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 289 
                 Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine 
               
               
                 290 
                 (2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 291 
                 (2,3-Dimethoxy-benzyl)-(8 fluoro-dibenzofuran-2-yl)-amine 
               
               
                 292 
                 (4-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 293 
                 (3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 294 
                 (4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 295 
                 (3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 296 
                 (2-Chloro-benzyl)-(8-fluoro-dibenzofuran 2-yl)-amine 
               
               
                 297 
                 4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 
               
               
                 298 
                 3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 
               
               
                 299 
                 Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine 
               
               
                 300 
                 (8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine 
               
               
                 301 
                 (8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 
               
               
                 302 
                 (8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine 
               
               
                 303 
                 (8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-benzyl)-amine 
               
               
                 304 
                 (8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-benzyl)-amine 
               
               
                 305 
                 (4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 306 
                 (4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 307 
                 (3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 308 
                 (2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 309 
                 (8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine 
               
               
                 310 
                 (8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine 
               
               
                 311 
                 Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine 
               
               
                 312 
                 Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine 
               
               
                 313 
                 Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine 
               
               
                 314 
                 (4-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 315 
                 Dibenzofuran-2-yl-(3-methyl-benzyl)-amine 
               
               
                 316 
                 (3-Chloro-benzyl)-dibenzofuran-2-yl-amine 
               
               
                 317 
                 3-(Dibenzofuran-2-ylaminomethyl)-phenol 
               
               
                 318 
                 (2-Chloro-benzyl)dibenzofuran-2-yl-amine 
               
               
                 319 
                 Dibenzofuran-2-yl-(3-methoxy-benzyl)-amine 
               
               
                 320 
                 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 
               
               
                 321 
                 (9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine 
               
               
                 322 
                 Dibenzofuran-4-yl-(2-methyl-benzyl)-amine 
               
               
                 323 
                 (6-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine 
               
               
                 324 
                 (2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 325 
                 Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine 
               
               
                 326 
                 Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine 
               
               
                 327 
                 Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine 
               
               
                 328 
                 Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine 
               
               
                 329 
                 Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine 
               
               
                 330 
                 (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine 
               
               
                 331 
                 Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine 
               
               
                 332 
                 (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 
               
               
                 333 
                 (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine 
               
               
                 334 
                 (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine 
               
               
                 335 
                 (8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2-ylmethyl)-amine 
               
               
                 336 
                 (8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine 
               
               
                 337 
                 (8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 
               
               
                 338 
                 (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 
               
               
                 339 
                 (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 
               
               
                 340 
                 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 341 
                 Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine 
               
               
                 342 
                 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 343 
                 (8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 344 
                 (8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 345 
                 (3,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 346 
                 (3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 347 
                 (3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 348 
                 (2,6-Difluoro-benzyl (2,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 349 
                 (2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 350 
                 (2,3 Difluoro-benzyl)-(8-fluoro-dibenzofiran 2-yl) r,ine 
               
               
                 351 
                 (2,5-Dimethyl benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 352 
                 (2,4-Dimethyl benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 353 
                 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 354 
                 (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 
               
               
                 355 
                 Dibenzofuran-2-yl-furan-2-ylmethyl-amine 
               
               
                 356 
                 Dibenzofuran-2-yl-furan-3-ylmethyl-amine 
               
               
                 357 
                 Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine 
               
               
                 358 
                 Dibenzofuran-2-yl-(4-methanesulfonyl-benzyl)-amine 
               
               
                 359 
                 Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine 
               
               
                 360 
                 Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine 
               
               
                 361 
                 Dibenzofuran-2-yl pyridin-2-ylmethyl-amine 
               
               
                 362 
                 Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 363 
                 Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzy)-amine 
               
               
                 364 
                 Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 365 
                 Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 366 
                 Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine 
               
               
                 367 
                 Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine 
               
               
                 368 
                 Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine 
               
               
                 369 
                 Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine 
               
               
                 370 
                 Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine 
               
               
                 371 
                 (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine 
               
               
                 372 
                 (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine 
               
               
                 373 
                 Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine 
               
               
                 374 
                 Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 375 
                 Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine 
               
               
                 376 
                 Benzyl-dibenzothiohen-2-yl-amine 
               
               
                 377 
                 Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine 
               
               
                 378 
                 Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine 
               
               
                 379 
                 Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine 
               
               
                 380 
                 Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine 
               
               
                 381 
                 Dibenzothiohen-2-yl-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 382 
                 (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine 
               
               
                 383 
                 Dibenzothiohen-2-yl-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-amine 
               
               
                 384 
                 Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 385 
                 Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine 
               
               
                 386 
                 Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine 
               
               
                 387 
                 Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine 
               
               
                 388 
                 Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine 
               
               
                 389 
                 Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine 
               
               
                 390 
                 Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine 
               
               
                 391 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 392 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl-benzyl)-amine 
               
               
                 393 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4-dimethyl-benzyl)-amine 
               
               
                 394 
                 (4-tert-Butyl-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 
               
               
                 395 
                 (2-Chloro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 
               
               
                 396 
                 (2,6-Difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 
               
               
                 397 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 398 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-fluoro-benzyl)-amine 
               
               
                 399 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3,5-dimethoxy-benzyl)-amine 
               
               
                 400 
                 Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 
               
               
                 401 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4-methoxy-benzyl)-amine 
               
               
                 402 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3-dimethoxy-benzyl)-amine 
               
               
                 403 
                 (2,5-difluoro-benzyl)-10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 
               
               
                 404 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-methoxy-benzyl)-amine 
               
               
                 405 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 406 
                 (2-Bromo-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 
               
               
                 407 
                 (2,3-Diydro-1,4-benzodioxin-6-ylmethyl)-(10,11-dihydro-5H- 
               
               
                   
                 dibenz[b,f]azepin-2-yl)-amine 
               
               
                 408 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 
               
               
                 409 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,5 dimethyl-benzyl)-amine 
               
               
                 410 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-thiophen-3-ylmethyl-amine 
               
               
                 411 
                 (10,11 -Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-1-ylmethyl-amine 
               
               
                 412 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-trifluoromethyl-benzyl)-amine 
               
               
                 413 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-2-ylmethyl-amine 
               
               
                 414 
                 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2 ethoxy-benzyl)-amine 
               
               
                 415 
                 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 416 
                 (2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 417 
                 (4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 418 
                 (2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 419 
                 (2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 420 
                 (10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine 
               
               
                 421 
                 (2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 422 
                 (3,S-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 423 
                 Benzyl-(10H-phenothiazin-2-yl)-amine 
               
               
                 424 
                 (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 425 
                 (2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 426 
                 (10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 427 
                 (2,3-Diydro-1,4-benzodioxin-6-ylmethyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 428 
                 (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 429 
                 (2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 
               
               
                 430 
                 (10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine 
               
               
                 431 
                 (10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-amine 
               
               
                 432 
                 (9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine 
               
               
                 433 
                 (9H Carbazol-3-yl)-(2-methyl-benzyl)-amine 
               
               
                 434 
                 (9H-Carbazo1-3-yl)-(2,4-methyl-benzyl)-amine 
               
               
                 435 
                 (4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine 
               
               
                 436 
                 (9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine 
               
               
                 437 
                 (9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine 
               
               
                 438 
                 (9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine 
               
               
                 439 
                 (9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine 
               
               
                 440 
                 (9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine 
               
               
                 441 
                 (9H-Carbazol-3-yl)-(2,5 difluoro-benzyl) amine 
               
               
                 442 
                 (9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine 
               
               
                 443 
                 (9H-Carbazol-3-yl)-(2,3 dihydro-1,4-benzodioxin-ylmethyl)-amine 
               
               
                 444 
                 (9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine 
               
               
                 445 
                 (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine 
               
               
                 446 
                 (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine 
               
               
                 447 
                 Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl-amine 
               
               
                 448 
                 Dibenzofuran-2-yl-bis-thiopen-3-ylmethyl-amine 
               
               
                 449 
                 Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine 
               
               
                 450 
                 2-Dibenzofuran,2-yl-2,3-dihydro-1H-isoindole 
               
               
                 451 
                 2-Dibenzofuran-2-yl-1H-isoindole-1,3-dione 
               
               
                 452 
                 Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine 
               
               
                 453 
                 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 
               
               
                 454 
                 Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine 
               
               
                 455 
                 Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine 
               
               
                 456 
                 Dibenzofuran-2-yl-(1-phenyl-butyl)-amine 
               
               
                 457 
                 Dibenzofuran-2-yl-phenethyl-amine 
               
               
                 458 
                 Dibenzofuran-2-yl-(1-phenyl-ethyl-amine 
               
               
                   
               
             
          
         
       
     
     EXAMPLES 
     
       
         
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                   
               
               
                   
                   
                 General 
                 M + H 
                 MOLECULAR 
               
               
                 Example 
                 MOLSTRUCTURE 
                 procedure 
                 (APCl)* 
                 FORMULA 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 1 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 282 
                 C18 H19 N O2 
               
               
                   
               
               
                 2 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 250 
                 C18 H19 H 
               
               
                   
               
               
                 3 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 250 
                 C18 H19 N 
               
               
                   
               
               
                 4 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 293 
                 C20 H24 N2 
               
               
                   
               
               
                 5 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 256 
                 C16 H17 N O2 
               
               
                   
               
               
                 6 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 314 
                 C18 H19 N O2S 
               
               
                   
               
               
                 7 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 310 
                 C20 H23 N O2 
               
               
                   
               
               
                 8 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 284 
                 C18 H21 N O2 
               
               
                   
               
               
                 9 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 270 
                 C17 H19 N O2 
               
               
                   
               
               
                 10 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7, 5 
                 308 
                 C20 H25 N3 
               
               
                   
               
               
                 11 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 371 
                 C26 H30 N2 
               
               
                   
               
               
                 12 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 265 
                 C18 H20 N2 
               
               
                   
               
               
                 13 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 328 
                 C24 H25 N 
               
               
                   
               
               
                 14 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 238 
                 C17 H19 N 
               
               
                   
               
               
                 15 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 346 
                 C18 H19 N O4S 
               
               
                   
               
               
                 16 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 322 
                 C22 H27 N O 
               
               
                   
               
               
                 17 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 320 
                 C22 H25 N O 
               
               
                   
               
               
                 18 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 318 
                 C22 H23 N O 
               
               
                   
               
               
                 19 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 348 
                 C24 H29 N O 
               
               
                   
               
               
                 20 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 278 
                 C19 H19 N O 
               
               
                   
               
               
                 21 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 322 
                 C22 H27 N O 
               
               
                   
               
               
                 22 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 292 
                 C20 H21 N O 
               
               
                   
               
               
                 23 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 252 
                 C17 H17 N O 
               
               
                   
               
               
                 24 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6, 5 
                 296 
                 C19 H21 N O2 
               
               
                   
               
               
                 25 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6, 5 
                 264 
                 C19 H21 N 
               
               
                   
               
               
                 26 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 4 
                 360 
                 C20 H25 N O S2 
               
               
                   
               
               
                 27 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 4 
                 324 
                 C22 H29 N O 
               
               
                   
               
               
                 28 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 4 
                 268 
                 C18 H21 N O 
               
               
                   
               
               
                 29 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 357 
                 C20 H24 N2 O2 S 
               
               
                   
               
               
                 30 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 267 
                 C18 H22 N2 
               
               
                   
               
               
                 31 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 325 
                 C20 H24 N2 S 
               
               
                   
               
               
                 32 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 307 
                 C21 H26 N2 
               
               
                   
               
               
                 33 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 321 
                 C22 H28 N2 
               
               
                   
               
               
                 34 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 295 
                 C20 H26 N2 
               
               
                   
               
               
                 35 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 293 
                 C20 H24 N2 
               
               
                   
               
               
                 36 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 281 
                 C19 H24 N2 
               
               
                   
               
               
                 37 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 224 
                 C16 H17 N 
               
               
                   
               
               
                 38 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 282 
                 C18 H19 N S 
               
               
                   
               
               
                 39 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 278 
                 C20 H23 N 
               
               
                   
               
               
                 40 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 316 
                 C17 H17 N O3 S 
               
               
                   
               
               
                 41 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 267 
                 C17 H18 N2 O 
               
               
                   
               
               
                 42 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 226 
                 C15 H15 N O 
               
               
                   
               
               
                 43 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 266 
                 C18 H19 N O 
               
               
                   
               
               
                 44 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 252 
                 C17 H17 N O 
               
               
                   
               
               
                 45 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 316 
                 C17 H17 N O3 S 
               
               
                   
               
               
                 46 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 267 
                 C17 H18 N2 O 
               
               
                   
               
               
                 47 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 226 
                 C15 H15 N O 
               
               
                   
               
               
                 48 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 284 
                 C17 H17 N O S 
               
               
                   
               
               
                 49 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 266 
                 C18 H19 N O 
               
               
                   
               
               
                 50 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 280 
                 C19 H21 N O 
               
               
                   
               
               
                 51 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 308, 310 
                 C19 H14 Cl N O 
               
               
                   
               
               
                 52 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 353. 355 
                 C19 H13 Cl N2 O3 
               
               
                   
               
               
                 53 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 358 
                 C20 H14 F3 N O2 
               
               
                   
               
               
                 54 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C20 H15 N O3 
               
               
                   
               
               
                 55 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 332 
                 C21 H17 N O3 
               
               
                   
               
               
                 56 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 57 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C20 H14 F3 N O 
               
               
                   
               
               
                 58 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 1, 2, 3 
                 288 
                 C20 H17 N O 
               
               
                   
               
               
                 59 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 280 
                 C17 H13 N O S 
               
               
                   
               
               
                 60 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C19 H14 N2 O3 
               
               
                   
               
               
                 61 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20 H17 N O S 
               
               
                   
               
               
                 62 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20 H17 N O 
               
               
                   
               
               
                 63 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 274 
                 C19 H15 N O 
               
               
                   
               
               
                 64 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 380 
                 C26 H21 N O2 
               
               
                   
               
               
                 65 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 330 
                 C23 H23 N O 
               
               
                   
               
               
                 66 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 332 
                 C22 H21 N O2 
               
               
                   
               
               
                 67 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 270 
                 C17 H19 N O2 
               
               
                   
               
               
                 68 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 268 
                 C18 H21 N O 
               
               
                   
               
               
                 69 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 254 
                 C17 H19 N O 
               
               
                   
               
               
                 70 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 268 
                 C18 H21 N O 
               
               
                   
               
               
                 71 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 294 
                 C20 H23 N O 
               
               
                   
               
               
                 72 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 294 
                 C20 H23 N O 
               
               
                   
               
               
                 73 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 280 
                 C19 H21 N O 
               
               
                   
               
               
                 74 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 284 
                 C17 H17 N O S 
               
               
                   
               
               
                 75 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 270 
                 C16 H15 N O S 
               
               
                   
               
               
                 76 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 254 
                 C17 H19 N O 
               
               
                   
               
               
                 77 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 254 
                 C17 H19 N O 
               
               
                   
               
               
                 78 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 240 
                 C16 H17 N O 
               
               
                   
               
               
                 79 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 293 
                 C18 H13 F N2 O 
               
               
                   
               
               
                 80 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 276 
                 C17 H13 N3 O 
               
               
                   
               
               
                 81 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 289 
                 C19 H16 N2 O 
               
               
                   
               
               
                 82 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 321 
                 C20 H17 F N2 O 
               
               
                   
               
               
                 83 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 354 
                 C23 H19 N3 O 
               
               
                   
               
               
                 85 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 381 
                 C21 H20 N2 O3 S 
               
               
                   
               
               
                 86 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 304 
                 C19 H17 N3 O 
               
               
                   
               
               
                 87 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 317 
                 C21 H20 N2 O 
               
               
                   
               
               
                 88 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3, 2 
                 355 
                 C23 H18 N2 S 
               
               
                   
               
               
                 89 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 383 
                 C20 H18 N2 O2 S 
               
               
                   
               
               
                 90 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 339 
                 C19 H15 F N2 O S 
               
               
                   
               
               
                 91 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 325 
                 C18 H13 F N2 O S 
               
               
                   
               
               
                 92 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 358 
                 C21 H15 N3 O S 
               
               
                   
               
               
                 93 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 357 
                 C22 H16 N2 O S 
               
               
                   
               
               
                 94 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 385 
                 C19 H16 N2 O3 S 
               
               
                   
               
               
                 95 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 308 
                 C17 H13 N3 O S 
               
               
                   
               
               
                 96 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 321 
                 C19 H16 N2 O S 
               
               
                   
               
               
                 97 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 335 
                 C24 H18 N2 
               
               
                   
               
               
                 98 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 362 
                 C22 H19 N O2 S 
               
               
                   
               
               
                 99 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 285 
                 C20 H16 N2 
               
               
                   
               
               
                 100 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 298 
                 C22 H19 N 
               
               
                   
               
               
                 101 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 322 
                 C20 H16 F N O2 
               
               
                   
               
               
                 102 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 308 
                 C19 H14 F N O2 
               
               
                   
               
               
                 103 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 341 
                 C22 H16 N2 O2 
               
               
                   
               
               
                 104 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 340 
                 C23 H17 N O2 
               
               
                   
               
               
                 105 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 368 
                 C20 H17 N O4 S 
               
               
                   
               
               
                 106 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 291 
                 C18 H14 N2 O2 
               
               
                   
               
               
                 107 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 322 
                 C20 H16 F N O2 
               
               
                   
               
               
                 108 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 308 
                 C19 H14 F N O2 
               
               
                   
               
               
                 109 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 368 
                 C20 H17 N O4 S 
               
               
                   
               
               
                 110 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 291 
                 C18 H14 N2 O2 
               
               
                   
               
               
                 111 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 304 
                 C20 H17 N O2 
               
               
                   
               
               
                 112 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 326, 328 
                 C19 H13 Cl F N O 
               
               
                   
               
               
                 113 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 359 
                 C23 H16 Cl N O 
               
               
                   
               
               
                 114 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 387 
                 C20 H16 Cl N O3 S 
               
               
                   
               
               
                 115 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 355 
                 C20 H22 N2 O2 S 
               
               
                   
               
               
                 116 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 278 
                 C18 H19 N3 
               
               
                   
               
               
                 117 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 307 
                 C19 H15 F N2 O 
               
               
                   
               
               
                 118 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 325 
                 C22 H16 N2 O 
               
               
                   
               
               
                 119 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C22 H16 N2 O 
               
               
                   
               
               
                 120 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 335 
                 C21 H19 F N2 O 
               
               
                   
               
               
                 121 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 317 
                 C21 H20 N2 O 
               
               
                   
               
               
                 122 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C17 H12 N2 O3 S 
               
               
                   
               
               
                 123 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 281 
                 C16 H12 N2 O S 
               
               
                   
               
               
                 124 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 292 
                 C19 H14 F N O 
               
               
                   
               
               
                 125 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21 H20N2O2 
               
               
                   
               
               
                 126 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C22H22N2O3 
               
               
                   
               
               
                 127 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C24H26N2O1 
               
               
                   
               
               
                 128 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 303 
                 C20H18N2O1 
               
               
                   
               
               
                 129 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C21H17N3O1 
               
               
                   
               
               
                 130 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C20H17N1O2S1 
               
               
                   
               
               
                 131 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338, 340 
                 C20H16N1O2Cl1 
               
               
                   
               
               
                 132 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C20H17O2S1N1 
               
               
                   
               
               
                 133 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 366 
                 C21H19O3N1S1 
               
               
                   
               
               
                 134 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 354 
                 C20H16O2N1S1F1 
               
               
                   
               
               
                 135 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 362 
                 C23H23O1N1S1 
               
               
                   
               
               
                 136 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C19H15N1O1S1 
               
               
                   
               
               
                 137 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350 
                 C21H19N1O2S1 
               
               
                   
               
               
                 138 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 368, 370 
                 C21H18N1O3Cl1 
               
               
                   
               
               
                 139 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 356, 358 
                 C20H15N1O2Cl1F1 
               
               
                   
               
               
                 140 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308, 310 
                 C19H14NOCl 
               
               
                   
               
               
                 141 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H19NO 
               
               
                   
               
               
                 142 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 315, 317 
                 C15H11N2OClS 
               
               
                   
               
               
                 143 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H19NO 
               
               
                   
               
               
                 144 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 332 
                 C22H21NO2 
               
               
                   
               
               
                 145 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C21H18NOF 
               
               
                   
               
               
                 146 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C24H25N 
               
               
                   
               
               
                 147 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 272 
                 C20H17N1 
               
               
                   
               
               
                 148 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 279 
                 C16H14N2S 
               
               
                   
               
               
                 149 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 316 
                 C22H21NO 
               
               
                   
               
               
                 150 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 151 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C20H13N2Ocl 
               
               
                   
               
               
                 152 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 153 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 154 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20H16NFO2 
               
               
                   
               
               
                 155 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 330 
                 C23H23NO 
               
               
                   
               
               
                 156 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C21H19NO2 
               
               
                   
               
               
                 157 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H20N2O2 
               
               
                   
               
               
                 158 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338, 340 
                 C20H16NO2Cl 
               
               
                   
               
               
                 159 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352, 354 
                 C21H18NO2Cl 
               
               
                   
               
               
                 160 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21 H19 N O 
               
               
                   
               
               
                 161 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309 
                 C18 H16 N2 O S 
               
               
                   
               
               
                 162 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C19 H17 N3 O 
               
               
                   
               
               
                 163 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 383, 385 
                 C19 H14 Br N O S 
               
               
                   
               
               
                 164 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C22 H16 N2 O S 
               
               
                   
               
               
                 165 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 312 
                 C17 H13 N O S2 
               
               
                   
               
               
                 166 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 321 
                 C19 H16 N2 O S 
               
               
                   
               
               
                 167 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C18 H14 N2 O S 
               
               
                   
               
               
                 168 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C18 H14 N2 O S 
               
               
                   
               
               
                 169 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 314, 316 
                 C17 H12 Cl N O S 
               
               
                   
               
               
                 170 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 379,  381 
                 C21 H19 Br N2 
               
               
                   
               
               
                 171 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323, 325 
                 C19 H15 Cl N2 O 
               
               
                   
               
               
                 172 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C19 H18 N2 S 
               
               
                   
               
               
                 173 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 341, 342 
                 C19 H17 Cl N2 S 
               
               
                   
               
               
                 174 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 3O2 
                 C20 H19 N3 
               
               
                   
               
               
                 175 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350, 352 
                 C20 H16 Br N 
               
               
                   
               
               
                 176 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 309, 311 
                 C18 H13 Cl N2 O 
               
               
                   
               
               
                 177 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323 
                 C23 H18 N2 
               
               
                   
               
               
                 178 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 278 
                 C18 H15 N S 
               
               
                   
               
               
                 179 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 287 
                 C20 H18 N2 
               
               
                   
               
               
                 180 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 273 
                 C19 H16 N2 
               
               
                   
               
               
                 181 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 273 
                 C19 H16 N2 
               
               
                   
               
               
                 182 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 273 
                 C19 H16 N2 
               
               
                   
               
               
                 183 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309, 311 
                 C18 H13 Cl N2 O 
               
               
                   
               
               
                 184 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C22 H16 N2 O 
               
               
                   
               
               
                 185 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C22 H16 N2 O 
               
               
                   
               
               
                 186 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 280 
                 C17 H13 N O S 
               
               
                   
               
               
                 187 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 289 
                 C19 H16 N2 O 
               
               
                   
               
               
                 188 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18 H14 N2 O 
               
               
                   
               
               
                 189 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18 H14 N2 O 
               
               
                   
               
               
                 190 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18 H14 N2 O 
               
               
                   
               
               
                 191 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 387, 389 
                 C19 H13 Br Cl N O 
               
               
                   
               
               
                 192 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309, 311 
                 C18 H13 Cl N2 O 
               
               
                   
               
               
                 193 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C20 H15 F3 N2 O 
               
               
                   
               
               
                 194 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C20 H15 F3 N2 O 
               
               
                   
               
               
                 195 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20 H16 F2 N2 O 
               
               
                   
               
               
                 196 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20 H16 F2 N2 O 
               
               
                   
               
               
                 197 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20 H16 F2 N2 O 
               
               
                   
               
               
                 198 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20 H16 F2 N2 O 
               
               
                   
               
               
                 199 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C22 H22 N2 O 
               
               
                   
               
               
                 200 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C22 H22 N2 O 
               
               
                   
               
               
                 201 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 361 
                 C22 H20 N2 O3 
               
               
                   
               
               
                 202 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338 
                 C20 H16 F N O S 
               
               
                   
               
               
                 203 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C19 H11 Cl F3 N O 
               
               
                   
               
               
                 204 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C19 H12 F3 N O S 
               
               
                   
               
               
                 205 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C19 H12 F3 N O S 
               
               
                   
               
               
                 206 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19 H13 F2 N O S 
               
               
                   
               
               
                 207 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19 H13 F2 N O S 
               
               
                   
               
               
                 208 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19 H13 F2 N O S 
               
               
                   
               
               
                 209 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19 H13 F2 N O S 
               
               
                   
               
               
                 210 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O S 
               
               
                   
               
               
                 211 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 364 
                 C21 H17 N O3 S 
               
               
                   
               
               
                 212 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 272 
                 C16 H14 F N S 
               
               
                   
               
               
                 213 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C19 H11 Cl F3 N O 
               
               
                   
               
               
                 214 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19 H12 Cl F2 N O 
               
               
                   
               
               
                 215 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19 H12 Cl F2 N O 
               
               
                   
               
               
                 216 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19 H12 Cl F2 N O 
               
               
                   
               
               
                 217 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C22 H21 F N2 
               
               
                   
               
               
                 218 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19 H12 Cl F2 N O 
               
               
                   
               
               
                 219 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 355 
                 C21 H17 F3 N2 
               
               
                   
               
               
                 220 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 355 
                 C21 H17 F3 N2 
               
               
                   
               
               
                 221 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21 H18 F2 N2 
               
               
                   
               
               
                 222 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21 H18 F2 N2 
               
               
                   
               
               
                 223 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21 H18 F2 N2 
               
               
                   
               
               
                 224 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21 H18 F2 N2 
               
               
                   
               
               
                 225 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23 H24 N2 
               
               
                   
               
               
                 226 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23 H24 N2 
               
               
                   
               
               
                 227 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C23 H22 N2 O2 
               
               
                   
               
               
                 228 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C21 H18 F N 
               
               
                   
               
               
                 229 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21 H18 Cl N O 
               
               
                   
               
               
                 230 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326 
                 C20 H14 F3 N 
               
               
                   
               
               
                 231 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326 
                 C20 H14 F3 N 
               
               
                   
               
               
                 232 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C20 H15 F2 N 
               
               
                   
               
               
                 233 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C20 H15 F2 N 
               
               
                   
               
               
                 234 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C20 H15 F2 N 
               
               
                   
               
               
                 235 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 300 
                 C22 H21 N 
               
               
                   
               
               
                 236 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 300 
                 C22 H21 N 
               
               
                   
               
               
                 237 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 330 
                 C22 H19 N O2 
               
               
                   
               
               
                 238 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336,  338 
                 C21 H18 Cl N O 
               
               
                   
               
               
                 239 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21 H19 N O 
               
               
                   
               
               
                 240 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C20 H16 F N O 
               
               
                   
               
               
                 241 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 335 
                 C21 H19 F N2 O 
               
               
                   
               
               
                 242 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 341 
                 C20 H15 Cl F N O 
               
               
                   
               
               
                 243 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 367 
                 C21 H16 Cl N O3 
               
               
                   
               
               
                 244 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 366 
                 C21 H19 N O3 S 
               
               
                   
               
               
                 245 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 366 
                 C21 H19 N O3 S 
               
               
                   
               
               
                 246 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340, 342 
                 C19 H14 Cl N O S 
               
               
                   
               
               
                 247 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C20 H17 N O2 S 
               
               
                   
               
               
                 248 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20 H17 N O S 
               
               
                   
               
               
                 249 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318, 320 
                 C21 H16 Cl N 
               
               
                   
               
               
                 250 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21 H16 F N 
               
               
                   
               
               
                 251 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350 
                 C21 H19 N O4 
               
               
                   
               
               
                 252 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 324, 326 
                 C19 H14 Cl N O2 
               
               
                   
               
               
                 253 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C19 H15 N O3 
               
               
                   
               
               
                 254 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20 H17 N O3 
               
               
                   
               
               
                 255 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 317 
                 C21 H20 N2 O 
               
               
                   
               
               
                 256 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C21 H19 F N2 
               
               
                   
               
               
                 257 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 315 
                 C22 H22 N2 
               
               
                   
               
               
                 258 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306, 308 
                 C20 H16 Cl N 
               
               
                   
               
               
                 259 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20 H17 N O 
               
               
                   
               
               
                 260 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 3O2 
                 C21 H19 N O 
               
               
                   
               
               
                 261 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340 
                 C21 H16 F3 N 
               
               
                   
               
               
                 262 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C20 H16 F N 
               
               
                   
               
               
                 263 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 264 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 265 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C19 H15 N O2 
               
               
                   
               
               
                 266 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20 H17 N O2 
               
               
                   
               
               
                 267 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 364 
                 C22 H21 N O4 
               
               
                   
               
               
                 268 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 364 
                 C22 H21 N O4 
               
               
                   
               
               
                 269 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 270 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 271 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20 H17 N O2 
               
               
                   
               
               
                 272 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 351, 353 
                 C19 H14 Br N O 
               
               
                   
               
               
                 273 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 282 
                 C16 H12 F N3 O 
               
               
                   
               
               
                 274 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 317 
                 C20 H13 F N2 O 
               
               
                   
               
               
                 275 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C21 H18 F N O2 
               
               
                   
               
               
                 276 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338 
                 C20 H16 F N O S 
               
               
                   
               
               
                 277 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 369, 371 
                 C19 H13 Br F N O 
               
               
                   
               
               
                 278 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 343 
                 C22 H15 F N2 O 
               
               
                   
               
               
                 279 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 343 
                 C22 H15 F N2 O 
               
               
                   
               
               
                 280 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 324 
                 C23 H17 N O 
               
               
                   
               
               
                 281 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C23 H16 F N O 
               
               
                   
               
               
                 282 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C23 H16 F N O 
               
               
                   
               
               
                 283 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C19 H14 N2 O3 
               
               
                   
               
               
                 284 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 264 
                 C16 H13 N3 O 
               
               
                   
               
               
                 285 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 299 
                 C20 H14 N2 O 
               
               
                   
               
               
                 286 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C21 H19 N O2 
               
               
                   
               
               
                 287 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C20 H14 F3 N O 
               
               
                   
               
               
                 288 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 330 
                 C23 H23 N O 
               
               
                   
               
               
                 289 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 292 
                 C19 H14 F N O 
               
               
                   
               
               
                 290 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352 
                 C21 H18 F N O3 
               
               
                   
               
               
                 291 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352 
                 C21 H18 F N O3 
               
               
                   
               
               
                 292 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 398 
                 C26 H20 F N O2 
               
               
                   
               
               
                 293 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 398 
                 C26 H20 F N O2 
               
               
                   
               
               
                 294 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326, 328 
                 C19 H13 Cl F N O 
               
               
                   
               
               
                 295 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326, 328 
                 C19 H13 Cl F N O 
               
               
                   
               
               
                 296 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326, 328 
                 C19 H13 Cl F N O 
               
               
                   
               
               
                 297 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C19 H14 F N O2 
               
               
                   
               
               
                 298 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 308 
                 C19 H14 F N O2 
               
               
                   
               
               
                 299 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 292 
                 C19 H14 F N O 
               
               
                   
               
               
                 300 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20 H16 F N O2 
               
               
                   
               
               
                 301 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20 H16 F N O2 
               
               
                   
               
               
                 302 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20 H16 F N O2 
               
               
                   
               
               
                 303 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C20 H13 F4 N O 
               
               
                   
               
               
                 304 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C20 H13 F4 N O 
               
               
                   
               
               
                 305 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 348 
                 C23 H22 F N O 
               
               
                   
               
               
                 306 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 307 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 308 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 309 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C20 H16 F N O 
               
               
                   
               
               
                 310 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C20 H16 F N O 
               
               
                   
               
               
                 311 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 312 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 313 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 314 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 380 
                 C26 H21 N O2 
               
               
                   
               
               
                 315 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20 H17 N O 
               
               
                   
               
               
                 316 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308, 310 
                 C19 H14 Cl N O 
               
               
                   
               
               
                 317 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C19 H15 N O2 
               
               
                   
               
               
                 318 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308, 310 
                 C19 H14 Cl N O 
               
               
                   
               
               
                 319 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20 H17 N O2 
               
               
                   
               
               
                 320 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20 H17 N O2 
               
               
                   
               
               
                 321 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 286 
                 C21 H19 N 
               
               
                   
               
               
                 322 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20 H17 N O 
               
               
                   
               
               
                 323 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 323 
                 C20 H16 Cl N O 
               
               
                   
               
               
                 324 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C20 H18 N2 S 
               
               
                   
               
               
                 325 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 304 
                 C20 H17 N O2 
               
               
                   
               
               
                 326 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 327 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 328 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 329 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 330 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 298 
                 C17 H12 F N O S 
               
               
                   
               
               
                 331 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21 H19 N O 
               
               
                   
               
               
                 332 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 298 
                 C17 H12 F N O S 
               
               
                   
               
               
                 333 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 282 
                 C17 H12 F N O2 
               
               
                   
               
               
                 334 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 282 
                 C17 H12 F N O2 
               
               
                   
               
               
                 335 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C19 H15 F N2 O 
               
               
                   
               
               
                 336 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 370 
                 C20 H16 F N O3 S 
               
               
                   
               
               
                 337 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 293 
                 C18 H13 F N2 O 
               
               
                   
               
               
                 338 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 293 
                 C18 H13 F N2 O 
               
               
                   
               
               
                 339 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 293 
                 C18 H13 F N2 O 
               
               
                   
               
               
                 340 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340 
                 C20 H15 F2 N O2 
               
               
                   
               
               
                 341 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21 H19 N O 
               
               
                   
               
               
                 342 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 324 
                 C20 H15 F2 N O 
               
               
                   
               
               
                 343 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 346 
                 C19 H11 F4 N O 
               
               
                   
               
               
                 344 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 346 
                 C19 H11 F4 N O 
               
               
                   
               
               
                 345 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 346 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 347 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 348 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 349 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 350 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 351 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C21 H18 F N O 
               
               
                   
               
               
                 352 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C21 H18 F N O 
               
               
                   
               
               
                 353 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350 
                 C21 H16 F N O3 
               
               
                   
               
               
                 354 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352 
                 C21 H18 F N O3 
               
               
                   
               
               
                 355 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 264 
                 C17 H13 N O2 
               
               
                   
               
               
                 356 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 264 
                 C17 H13 N O2 
               
               
                   
               
               
                 357 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 289 
                 C19 H16 N2 O 
               
               
                   
               
               
                 358 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 352 
                 C20 H17 N O3 S 
               
               
                   
               
               
                 359 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 275 
                 C18 H14 N2 O 
               
               
                   
               
               
                 360 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18 H14 N2 O 
               
               
                   
               
               
                 361 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18 H14 N2 O 
               
               
                   
               
               
                 362 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20 H16 F N O2 
               
               
                   
               
               
                 363 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 306 
                 C20 H16 F N O 
               
               
                   
               
               
                 364 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 365 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19 H12 F3 N O 
               
               
                   
               
               
                 366 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 367 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19 H13 F2 N O 
               
               
                   
               
               
                 368 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21 H19 N O3 
               
               
                   
               
               
                 369 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NS 
               
               
                   
               
               
                 370 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C21H19NS 
               
               
                   
               
               
                 371 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 346 
                 C23H23NS 
               
               
                   
               
               
                 372 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323, 325 
                 C19H14ClNS 
               
               
                   
               
               
                 373 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326 
                 C19H13F2NS 
               
               
                   
               
               
                 374 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 344 
                 C19H12F3NS 
               
               
                   
               
               
                 375 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C19H14FNS 
               
               
                   
               
               
                 376 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C19H15NS 
               
               
                   
               
               
                 377 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20H17NOS 
               
               
                   
               
               
                 378 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350 
                 C21H19NO2S 
               
               
                   
               
               
                 379 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326 
                 C19H13F2NS 
               
               
                   
               
               
                 380 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20H17NOS 
               
               
                   
               
               
                 381 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 344 
                 C19H12F3NS 
               
               
                   
               
               
                 382 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 369 
                 C19H14BrNS 
               
               
                   
               
               
                 383 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 348 
                 C21H17NO2S 
               
               
                   
               
               
                 384 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338 
                 C20H16FNOS 
               
               
                   
               
               
                 385 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C21H19NS 
               
               
                   
               
               
                 386 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 296 
                 C17H13NS2 
               
               
                   
               
               
                 387 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340 
                 C23H17NS 
               
               
                   
               
               
                 388 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 358 
                 C20H14F3NS 
               
               
                   
               
               
                 389 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340 
                 C23H17NS 
               
               
                   
               
               
                 390 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NOS 
               
               
                   
               
               
                 391 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C22H21FN2 
               
               
                   
               
               
                 392 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 315 
                 C22H22N2 
               
               
                   
               
               
                 393 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23H24N2 
               
               
                   
               
               
                 394 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C25H28N2 
               
               
                   
               
               
                 395 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334, 336 
                 C21H19ClN2 
               
               
                   
               
               
                 396 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18F2N2 
               
               
                   
               
               
                 397 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 355 
                 C21H17F3N2 
               
               
                   
               
               
                 398 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C21H19FN2 
               
               
                   
               
               
                 399 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 361 
                 C23H24N2O2 
               
               
                   
               
               
                 400 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 301 
                 C21H20N2 
               
               
                   
               
               
                 401 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C22H22N2O 
               
               
                   
               
               
                 402 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 361 
                 C23H24N2O2 
               
               
                   
               
               
                 403 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18F2N2 
               
               
                   
               
               
                 404 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C22H22N2O 
               
               
                   
               
               
                 405 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 355 
                 C21H17F3N2 
               
               
                   
               
               
                 406 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 380 
                 C21H19BrN2 
               
               
                   
               
               
                 407 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C23H22N2O2 
               
               
                   
               
               
                 408 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 349 
                 C22H21FN2O 
               
               
                   
               
               
                 409 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23H24N2 
               
               
                   
               
               
                 410 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C19H18N2S 
               
               
                   
               
               
                 411 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 351 
                 C25H22N2 
               
               
                   
               
               
                 412 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 369 
                 C22H19F3N2 
               
               
                   
               
               
                 413 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 351 
                 C25H22N2 
               
               
                   
               
               
                 414 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C23H24N2O 
               
               
                   
               
               
                 415 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C20H17FN2S 
               
               
                   
               
               
                 416 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H20N2S 
               
               
                   
               
               
                 417 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 361 
                 C23H24N2S 
               
               
                   
               
               
                 418 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338, 340 
                 C19H15ClN2S 
               
               
                   
               
               
                 419 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 341 
                 C19H14F2N2S 
               
               
                   
               
               
                 420 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C19H13F3N2S 
               
               
                   
               
               
                 421 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323 
                 C19H15FN2S 
               
               
                   
               
               
                 422 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 365 
                 C21H20N2O2S 
               
               
                   
               
               
                 423 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 305 
                 C19H16N2S 
               
               
                   
               
               
                 424 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 335 
                 C20H18N2OS 
               
               
                   
               
               
                 425 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 341 
                 C19H14F2N2S 
               
               
                   
               
               
                 426 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C19H13F3N2S 
               
               
                   
               
               
                 427 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C21H18N2O2S 
               
               
                   
               
               
                 428 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 353 
                 C20H17FN2OS 
               
               
                   
               
               
                 429 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H2ON2S 
               
               
                   
               
               
                 430 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 311 
                 C17H14N2S2 
               
               
                   
               
               
                 431 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 373 
                 C20H15F3N2S 
               
               
                   
               
               
                 432 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 305 
                 C20H17FN2 
               
               
                   
               
               
                 433 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 287 
                 C20H18N2 
               
               
                   
               
               
                 434 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 301 
                 C21H20N2 
               
               
                   
               
               
                 435 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23H24N2 
               
               
                   
               
               
                 436 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306, 308 
                 C19H15ClN2 
               
               
                   
               
               
                 437 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309 
                 C19H14F2N2 
               
               
                   
               
               
                 438 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 327 
                 C19H13F3N2 
               
               
                   
               
               
                 439 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H20N2O2 
               
               
                   
               
               
                 440 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H20N2O2 
               
               
                   
               
               
                 441 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309 
                 C19H14F2N2 
               
               
                   
               
               
                 442 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 327 
                 C19H13F3N2 
               
               
                   
               
               
                 443 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C21H18N2O2 
               
               
                   
               
               
                 444 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 301 
                 C21H20N2 
               
               
                   
               
               
                 445 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323 
                 C23H18N2 
               
               
                   
               
               
                 446 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323 
                 C23H18N2 
               
               
                   
               
               
                 *Analysis was done by LCMS. Number shown is M + 1. In all cases mass shown agrees with the expected mass for the compound shown.  
               
             
          
         
       
     
     The following compounds were prepared according to the general procedure 1: 
     
       
         
               
               
               
               
               
             
           
               
                   
               
               
                   
                   
                 MS 
                   
                   
               
               
                   
                   
                 (M + H) 
                   1 H-NMR in CDCl 3  unless 
                 Mp 
               
               
                 Example 
                 Structure 
                 APCI 
                 otherwise noted (δ) 
                 (° C.) 
               
               
                   
               
             
             
               
                  26 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 360 
                 7.90(1H, d); 7.51(1H, d); 7.44-7.26(4H, m); 6.95(1H, d); 3.46(4H, t); 2.58(4H, t); 2.12(6H, s); 1.91(4H, quintet) 
                 — 
               
               
                   
               
               
                  55 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 332 
                 7.87(1H, d); 7.52(1H, d); 7.38-7.46(2H, quartet); 7.25-7.35(1H, t); 7.14(1H, s); 6.97-6.86(3H, m); 6.76-6.81(1H, d); 4.31 (2H, s) 4.25(4H, br s) 
                 — 
               
               
                   
               
               
                 447 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 480 
                 7.81(1H, d); 7.48(1H, d); 7.34-7.41(2H, m); 7.22-7.28(2H, t); 6.88-6.92(1H, d); 6.74-6.86(6H, m); 4.56(4H, br s); 4.23(8H, br s) 
                 — 
               
               
                   
               
               
                 448 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 376 
                 7.85(1H, d); 7.51(1H, d); 7.26-7.42(6H, m); 7.08(2H, br s); 6.99-7.06(3H, m); 4.60(4H, br s) 
                 109- 110 
               
               
                   
               
               
                  59 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 280 
                 7.86(1H, d); 7.52(1H, d); 7.38-7.44(2H, m); 7.25-7.35(3H, m); 7.19(1H, s); 7.14(1H, s); 6.81(1H, s); 4.43(2H, s) 
                 62-63 
               
               
                   
               
               
                  56 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 334 
                 7.86(1H, d); 7.52(1H, d); 7.29-7.42(3H, m); 7.12(1H, s); 6.78(1H, d); 6.60(2H, s); 6.41(1H, t); 4.35(2H, s); 3.79(6H, s) 
                 87-88 
               
               
                   
               
               
                  63 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 274 
                 7.89(1H, d); 7.53(1H, d); 7.31-7.48(8H, m); 7.18(1H, s); 6.81(1H, d); 4.43(2H, s); 4.10(1H, br s) 
                 81-82 
               
               
                   
               
               
                  61 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 320 
                 IN DMSO 7.93(1H, d); 7.54(1H, d); 7.17-7.42(8H, m); 6.81(1H, d); 6.22(1H, t); 4.30(2H, d); 2.41(3H, s) 
                 103- 104 
               
               
                   
               
               
                  73 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 294 
                 7.90(1H, d); 7.51(1H, d); 7.36-7.44(2H, quartet); 7.26-7.33(1H, t); 7.09(1H, s); 6.72(1H, d); 3.60(2H, br m); 1.95(2H, br m); 1.61 (12H, br m) 
                 50-52 
               
               
                   
               
               
                  57 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 342 
                 7.86(1H, d); 7.63(2H, d); 7.54(3H, t); 7.43(2H, quartet); 7.32(1H t); 7.11(1H, s); 6.77(1H, d); 4.46(2H, s) 4.15(1H, br s) 
                 89-90 
               
               
                   
               
               
                 449 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 364 
                 7.90(1H, d); 7.53(1H, d); 7.30-7.45(7H, m); 7.03-7.18(6H, m); 6.81(1H, d); 4.39(2H, s); 4.08(1H, br s) 
                 91-93 
               
               
                   
               
               
                 450 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 286 
                 7.96(1H, d); 7.31-7.55(8H, m); 7.15(1H, s); 6.83(1H, d); 4.73(4H, s) 
                 193- 195 
               
               
                   
               
               
                 451 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 314 
                 IN DMSO 8.22(1H, s); 8.13(1H, d); 7.84-8.01(5H, m); 7.75(1H, d); 7.57(2H, m); 7.43(1H, t) 
                 217- 218 
               
               
                   
               
               
                  58 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 288 
                 7.95(1H, d); 7.57(1H, d); 7.28-7.41(4H, m); 7.12-7.20(4H, m); 6.87(1H, d); 6.03(1H, t); 4.28(2H, d); 2.36(3H, s) 
                 84-85 
               
               
                   
               
               
                 452 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 358 
                 7.85(1H, d); 7.37-7.53(5H, m); 7.20-7.31(3H, m); 7.14(1H, s); 6.90(1H, d); 4.43(2H, s); 4.22(1H, br s) 
                 75-77 
               
               
                   
               
               
                 453 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 290 
                 7.86(1H, d); 7.55(1H, d); 7.41-7.47(3H, t); 7.18-7.34(4H, m); 6.89-7.02(3H, m); 4.52(2H, s) 
                 145- 147 
               
               
                   
               
               
                 454 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 366 
                 7.85(1H, d); 7.51(1H, d); 7.26-7.44(6H, m); 7.17(1H, d); 7.06-7.13(3H, m); 6.99-7.02(2H, m); 6.95(1H, s); 6.77(1H, dd) 4.40(2H, s); 4.17(1H, s) 
                 93-94 
               
               
                   
               
               
                  54 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 316 
                 7.86(1H, d); 7.51(1H, d); 7.26-7.43(3H, m); 7.14(1H, s); 6.87-6.92(2H, m); 6.77-6.81(2H, m); 5.96(2H, s); 4.32(2H, s); 4.12(1H, br s) 
                 85-86 
               
               
                   
               
               
                 455 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 302 
                 7.99(1H, d); 7.52(1H, d); 7.44-7.39(2H, m); 7.32-7.15(6H, m);  6.89(1H, s); 4.52(2H, s); 3.09(3H, s); 2.37(3H, s) 
               
               
                   
               
               
                 456 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 316 
                 7.77(1H, d); 7.48-7.21(9H, m); 7.00(1H, d); 6.70(1H, dd); 4.40(1H, t); 4.13(1H, br s) 1.88-1.78(2H, m); 1.51-1.38(2H, m); 0.97(3H, t) 
                 — 
               
               
                   
               
               
                 457 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 392 
                 7.87(1H, d); 7.53-7.26(9H, m); 7.16(1H, d); 6.77(1H, dd); 3.50(2H, t); 3.00(2H, t) 
                 — 
               
               
                   
               
               
                 458 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 288 
                 7.76(1H, d); 7.48-7.21(9H, m); 6.99(1H, d); 6.70(1H, dd); 4.57(1H, q); 4.07(1H, br s); 1.57(3H, d) 
                 94-95 
               
               
                   
               
               
                 202 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 338 
                 7.09(4H, m), 7.09(3H, m), 6.96(1H, d), 6.30(2H, m), 4.26(sH, s), 2.26(3H, s) 
                 — 
               
               
                   
               
               
                 210 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 334 
                 7.26(1H, s), 7.18(1H, d), 7.09(s, 1H), 7.07(1H, s), 7.02(1H, s), 6.95(1H, s), 6.97(2H, s), 6.96(1H, s), 6.87(1H, d), 6.36(1H, s), 6.34(1H, d), 4.2(2H, s), 2.31 (6H, s). 
                 — 
               
               
                   
               
               
                 135 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 362 
                 7.26(1H, s), 7.18(1H, d), 7.09(s, 1H), 7.07(1H, s), 7.02(1H, s), 6.95(1H, s), 6.97(2H, s), 6.96(1H, s), 6.87(1H, d), 6.36(1H, s), 6.34(1H, d), 4.2(2H, s), 1.3(9H, s). 
                 — 
               
               
                   
               
               
                 146 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 328 
                 7.61(d, 1H), 7.58(d, 1H), 7.45(d, 1H), 7.39(d, 1H), 7.37(s, 1H), 7.34(s, 1H), 7.32(s, 1H), 7.28(d, 1H), 7.16(t, 1H), 6.86(s, 1H), 6.68(dd, 1H), 4.35(s, 3H), 3.8(s, 2H), 1.31(s, 9H). 
                 — 
               
               
                   
               
               
                  90 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 339 
                 8.15(d, 1H), 7.22(s, 1H), 7.05(m, 3H), 6.98(m, 2H), 6.88(d, 1H), 6.32(d, 1H), 6.29(s, 1H), 4.3(s, 2H), 2.3(s, 3H). 
                 — 
               
               
                   
               
             
          
         
       
     
     Antiviral Activity Assays: 
     Screening assays: Anti-herpes simplex virus 1 (HSV) activity is determined in a yield reduction assay utilizing a recombinant HSV (HSV US3:: pgC-lacZ) which expresses  E. coli  β-galactosidase (β-gal) under the control of an HSV late gene promoter (Fink, D. J.; Sternberg, L. R.; Weber, P. C.; Mata, M; Goins, W. F.; Glorioso, J. C. Human Gene Therapy 3:11-19, 1992). Vero (African Green Monkey kidney) cells are infected at a multiplicity of infection of 0.01 with the virus, and serial dilutions of the compound in dimethyl sulfoxide (DMSO) are added. The final concentration of DMSO in all wells is 1%. DMSO is added to control wells. The infection is allowed to proceed for 2 days at which time the β-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The EC 50  is defined as the concentration of drug that produces a 50% reduction in β-gal production relative to control wells. 
     Anti-human cytomegalovirus (HCMV) activity is determined in a yield reduction assay utilizing a recombinant HCMV (RC256) that produces β-gal (Spaete, R. R.; Mocarski, E. S. Proceedings of the National Academy of Sciences USA 84:7213-7217, 1987). Primary human diploid fibroblasts (HFF cells) are infected at an moi of 0.01 with RC256, and serial dilutions of the compound in DMSO are added. The final concentration of DMSO in all wells is 1%. The infection is allowed to proceed for 7 days at which time the β-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The EC 50  is defined as the concentration of compound that produces a 50% reduction in β-gal production relative to control wells. TC 50  is defined as concentration of compound that produces cytotoxicity in 50% of uninfected cells. 
     Secondary yield reduction assays: To determine the activity of compounds against HSV, Vero cells are plated in 6 well dishes at a density of 5×10 5  cells/well. Cells are infected at a multiplicity of infection of 0.01 with HSV (strain Syn17+). 30 μL of one of six threefold serial dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37° C. incubator and the infection allowed to proceed for 2 days. Aliquots of the supernatant are harvested, and the virus titer determined. Vero cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to absorb to the monolayer for 1.5 hours, after which it is aspirated and replaced with growth medium containing 0.5% methylcellulose. Plaques are allowed to develop for 5 days, at which time the medium aspirated and the monolayer stained with crystal violet. The plaques are enumerated under law power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone. 
     To determine the activity of compounds against CMV, HFF cells, plated in 24 well plates at 1×10 5  cells/well, are infected with CMV (strain AD169) at an moi of 0.01. 10 μL of one of six threefold dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37° C. incubator and the infection allowed to proceed for 7 days. Aliquots of the supernatant of infected cells are harvested and the virus titer determined. HFF cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the cells for 2 hours, at which time the inoculum is aspirated and replaced with growth medium containing 0.5% methylcellulose. The plaques are allowed to develop for 7-10 days, at which time the medium is aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone. 
     Cellular toxicity assays: Cellular toxicity is measured in HFF cells. Cells are plated in 96 well plates at 1×10 4  cells/well. Serial dilutions of compounds are added to the wells in DMSO, with the final concentration of DMSO in all wells at 1%, in a total volume of 200 μL. The plates are maintained in a 37° C. incubator for 7 days. 50 μL of a solution of XTT (sodium-3′[1-(phenyl-amino-carbonyl)-3,-tetrazolium]-bis(bis(4-methoxy-6-nitro)-benzene sulfonic acid hydrate) (3×10 −4  mg/ml) is added to each well, and the plates returned to the incubator for 4 hours, after which the A 450  (absorbance at wavelength of 450 nm) for each well is measured in a plate reader. (Roehm, N. W., et al J. Immunol. Meth. 142:257-265, 1991). Toxicity is determined by comparison of the OD (optical density) of a well containing compound to the OD of wells containing DMSO only. 
     The effect of test compounds on cellular DNA synthesis is measured in a  14 C-thymidine incorporation assay, utilizing scintillation proximity assay technology. Cells are plated at 2×10 4  cells/well in Amersham Cytostar 96 well scintillating microplates. The following day, serial dilutions of test compounds in DMSO are added to the wells, along with 0.1 μCi/well of [methyl- 14 C]-thymidine (specific activity 50-62 mCi/mmol). The plates are counted immediately in a μBeta scintillation counter (Wallac), to determine background, then placed in a 37° C. incubator for 7 days. The plates are removed from the incubator at intervals and the thymidine incorporation into the cellular DNA determined by scintillation counting. Percent inhibition is determined by comparing  14 C incorporation in wells containing test compound to incorporation in wells containing DMSO only. 
     Table 3 contains the results of the antiviral efficacy (HSV: EC 50 , TC 50  and TI) screening results, where TI is the therapeutic index (TC 50 /EC 50 ). 
     
       
         
               
             
               
               
             
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                                                      TABLE 3 
               
             
             
               
                   
               
               
                  Antiviral Efficacy in a Yield Reduction Assay (HSV-1) 
               
             
          
           
               
                   
                 Antiviral Efficacy (Vero Cells) 
               
             
          
           
               
                   
                 Example 
                 EC 50  (μM) 
                 TC 50  (μM) 
                 TI (EC 50 /TC 50 ) 
               
               
                   
                   
               
             
          
           
               
                   
                  60 
                 0.5 
                 &gt;100 
                 &gt;200 
               
               
                   
                  57 
                 0.81 
                 &gt;100 
                 &gt;124 
               
               
                   
                  56 
                 0.7 
                 &gt;100 
                 &gt;143 
               
               
                   
                 208 
                 0.26 
                 &gt;100 
                 &gt;385 
               
               
                   
                 217 
                 0.32 
                 &gt;100 
                 &gt;313 
               
               
                   
                 139 
                 0.4 
                 &gt;100 
                 &gt;250 
               
               
                   
                 150 
                 0.85 
                 &gt;100 
                 &gt;118 
               
               
                   
                  93 
                 1.3 
                 &gt;100 
                 &gt;77 
               
               
                   
                 Reference 
                 0.2 
                 &gt;100 
                 &gt;500 
               
               
                   
                 Agent 
               
               
                   
                 (Acyclovir) 
               
               
                   
                   
               
             
          
         
       
     
     Table 4 contains the results of the antiviral efficacy (HSV: EC 50 , TC 50  and TI) screening results, where TI is the therapeutic index TC 50 /EC 50 ). 
     
       
         
               
             
               
               
             
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                                                      TABLE 4 
               
             
             
               
                   
               
               
                 Antiviral Efficacy in a Yield Reduction Assay (CMV) 
               
             
          
           
               
                   
                 Antiviral Efficacy (HFF Cells) 
               
             
          
           
               
                   
                 Example 
                 EC 50  (μM) 
                 TC 50  (μM) 
                 TI (EC 50 /TC 50 ) 
               
               
                   
                   
               
             
          
           
               
                   
                 61 
                 2.9 
                 &gt;100 
                 &gt;35 
               
               
                   
                 57 
                 1.7 
                 &gt;100 
                 &gt;59 
               
               
                   
                 65 
                 3.0 
                 &gt;100 
                 &gt;33 
               
               
                   
                 60 
                 1.3 
                 &gt;100 
                 &gt;77 
               
               
                   
                 Reference 
                 2.6 
                 &gt;100 
                 &gt;39 
               
               
                   
                 Agent 
               
               
                   
                 (Ganciclovir) 
               
               
                   
                   
               
             
          
         
       
     
     Tables 3 and 4 indicates that the compounds of the present invention have good to excellent activity in HSV infected cells from HSV pathogenecity at μM to sub-μM concentrations. 
     While the forms of the invention herein disclosed constitute presently preferred embodiments, many others are possible. It is not intended herein to mention all of the possible equivalent forms or ramifications of the invention. It is understood that the terms used herein are merely descriptive, rather than limiting, and that various changes may be made without departing from the spirit or scope of the invention.