bluuebunny/crossref_metadata_2025_split huggingface dataset:
New NO‐Donors with Antithrombotic and Vasodilating Activities, V: Oligonitroso Sydnone Imines
Authors: Rehse Klaus , Schleifer Klaus‐Jürgen , Martens Antje , Kämpfe Michael 
Published: October 2006

AbstractNine 4,4′‐bis‐ and four 4,4′‐tris‐N‐nitroso sydnone imines were synthesized. The sydnone imine moiety is connected either by aromatic 1,3‐phenylene or 1,3,5‐benzene or aliphatic methylene or propylene bridges. Compared to the corresponding sydnone imines the collagen induced platelet aggregation inhibiting activity is increased by several orders of magnitude by the nitroso derivatives. The most potent compound bears a hexyl substituent in 3‐position (1d: IC50 = 0.05 μmol/L). These data show that aromatic bridges (1d, 2d) are more favourable than aliphatic ones (4b). This indicates the mutual influence of the nitroso‐imino moieties via the aromatic bridges. In the series of 3,3′‐bis‐nitrososydnone imines (13 compounds) mostly additive effects of the nitroso groups are seen. The activities range from IC50 = 0.2 μmol/L (5i; 1,3‐xylene bridge) to IC50 = 8 μmol/L (5b; trimethylene bridge). The differences suggest different affinities to the platelet membrane.
Platelet Aggregation Inhibiting and Anticoagulant Effects of Oligoamines, XVIII: Oligoamines with Fluorescent Properties, Part B: Fluorophores in the Molecular Periphery
Authors: Rehse K. , Seidel T. 
Published: October 2006

AbstractSeventeen N,N′‐benzene‐1,3‐dimethane and nine N,N′,N″‐benzene‐1,3,5‐trimethane derivatives with fluorescent properties have been synthesized. Three of them show antiplatelet activities (inducer collagen, IC50 Born‐test) in concentrations < 10 μmol/L. They are suitable for interaction studies with biological macromolecules and synthetical and biological membranes. Structure activity relationships demonstrate that heteropolycyclic fluorophores i.e. quinoline, dibenzofurane, or carbazole are favorable substituents for this purpose.
Oxidationen an Thiourethanen, 12. Mitt.: Oxidative Desulfurierung von Cyclischen Dithiocarbamaten und ‐carbazaten mittels Wasserstoffperoxid oder Wasserstoffperoxid/Natriumwolframat im Zweiphasen‐System
Authors: Hanefeld Wolfgang , Schlitzer Martin 
Published: October 2006

AbstractCyclische Dithiocarbamate und ‐carbazate wurden im Zweiphasensystem mittels H2O2 mit und ohne Zusatz von Na2WO4 zu den entsprechenden 2‐Oxo‐Analogen desulfuriert.
3‐Substituierte 2‐Phenylindole: Synthese und biologische Eigenschaften
Authors: Mahboobi Siavosh , Grothus Götz , Angerer Erwin Von 
Published: October 2006

AbstractKnoevenagel‐Reaktion von Indol‐3‐carbaldehyden 5a,b und 7a,b mit Nitromethan führt zu den Nitroethenen 12 und 14, die analoge Reaktion mit Malodinitril zu den Methylidenmalonsäuredinitrilen 16.‐ Michael‐ Addition von Nitromethan an 12 und 14 führt zu den 1,3‐Dinitropropanen 13 und 15, Reduktion von 16 zu den Methylenmalonsäuredinitrilen 17.‐ Umsetzungen der Indole 3 mit n‐BuLi/Phenylsulfonylchlorid führen zu den 3‐Chlorindolen 18, Reaktion mit NaH/Ethyliodid sowie Etherspaltung und Acylierung zu den Acetoxyderivaten 19.‐ Verbindungen 7–11, 14–17 und 19 zeigen eine Affinität zum Estrogenrezeptor. Verbindungen 7b, 9–11, 17b und 19b hemmen das Wachstum von MCF‐7‐ und MDA‐MB‐231‐Zellen. IC50‐Werte werden bestimmt und Struktur‐Wirkungs‐Beziehungen diskutiert.
Nonsteroidal Antiinflammatory Agents, XVIII: C‐5 Functionalized 6,7‐Diphenyl‐2,3‐dihydro‐1H‐pyrrolizines as Inhibitors of Bovine Cyclooxygenase and 5‐Lipoxygenase
Authors: Dannhardt G. , Kiefer W. 
Published: October 2006

Abstract6‐(4‐Chlorophenyl)‐7‐phenyl‐2,3‐dihydro‐1H‐pyrrolizines with functional groups at position 5 of the heterocyclic moiety were synthesized and tested. To determine their antiinflammatory activity bovine blood was used as enzyme source for the cyclooxygenase and 5‐lipoxygenase, respectively. The iminoxy acetic acid derivative and the iminotetrazole selectively inhibit the 5‐lipoxygenase, all the other compounds show medium or low affinity to the active sites of cyclooxygenase and 5‐lipoxygenase. In general all compounds inhibit 5‐lipoxygenase more effectively than cyclooxygenase. Concerning the inhibition of 5‐lipoxygenase the most active compounds found are equipotent to the corresponding propionic acid compounds, but they aren't well balanced dual inhibitors as shown for the carboxylic derivatives. A structure activity relationship and the enzyme selectivity are discussed.
Synthesis and Antiviral Evaluation of Hydantoin Analogues of AZT
Authors: El‐Barbary Ahmed A. , Khodair Ahmed I. , Pedersen Erik B. 
Published: October 2006

Abstract3′‐Azidonucleosides 4 have been synthesized by condensation of silylated (Z)‐5‐ethylidenehydantoin and (Z)‐5‐benzylidenehydantoin with methyl 3‐azido‐5‐O‐tert‐butyldiphenylsilyl‐2,3‐dideoxy‐D‐erythro‐pentofuranoside (3). The nucleosides 4 were deblocked on treatment with tetrabutylammonium fluoride. The ethylidene group isomerized from Z to E configuration during the nucleoside synthesis. The new nucleosides did not show any appreciable activities against HIV‐1 or HSV‐1.
Constituents of Tropical Medicinal Plants, LXIII: Synthesis of 2‐Methoxyonychine Alkaloids ‐ Structure Revision of Oxylopidine
Authors: Achenbach Hans , Schwinn Andreas 
Published: October 2006

AbstractCondensation of β‐aminocinnamic acid esters with 3‐chloro‐2‐methoxy‐crotonaldehyde opened an easy access to 2‐phenyl‐5‐methoxy‐4‐methylnicotinic acid esters which were cyclized by polyphosphoric acid to yield the corresponding 2‐methoxyonychines. By this method a number of 2‐methoxy‐substituted onychines were prepared for the first time, i.a. oxylopidine, the structure of which has to be revised.
Herstellung und Reaktionsverhalten eines schwefelverbrückten Bischinolons
Authors: Löwe Werner , Kietzmann Annette 
Published: October 2006

AbstractAusgehend vom tosylierten Enaminon 5 lassen sich mit Essigsäure, Sulfurylchlorid und Thionylchlorid die neuen Chinolon‐Derivate 3, 8, 9 und 10 herstellen. Das schwefelverbrückte Bischinolon 8 gibt bei der Alkylierung die N‐Alkylprodukte 11 und 12. Die Dehydratisierung von 8 führt zum neuen Heterocyclus 13. Aus Verbindung 8 entsteht mit POCI3 das 4‐Chlorchinolin‐Derivat 14, aus dem das Sulfoxid 15 herstellbar ist. Verbindung 14 reagiert mit Thioharnstoff zum Isothiuroniumsalz 16. Dieses kann entweder durch Erhitzen oder über das Thion 17 nach H2S‐Eliminierung in das Dithiinobischinolin 18 übergeführt werden.
Anti‐inflammatory Activity of Amine‐carboxyboranes in Rodents
Authors: Hall Iris H. , Rajendran K. G. , Chen S. Y. , Wong Oi T. , Sood A. , Spielvogel B. F. 
Published: October 2006

AbstractAmine‐carboxyboranes are potent anti‐inflammatory agents reducing induced edema and pleural effusion at 8 mg/Kg, i.p. They protect against LPS (Salmonella) induced septic shock from 2–8 mg/Kg/day and are effective in blocking pain mediated both locally and centrally. The mode of action of these agents is by blocking release of cytokines from macrophages, thus reducing lysosomal hydrolytic and proteolytic enzyme activities of affected cells. The agents also reduce prostaglandin and leukotriene synthesis by blocking the activities of regulatory enzymes of the respective pathways.
Synthesis of 4‐Methylthio Analogues of FLT and AZT and their Evaluation against HIV
Authors: Abdel‐Rahman Adel A.‐H. , Abdel‐Bary Hamed M. , Pedersen Erik B. , Nielsen Claus 
Published: October 2006

AbstractSilylated 4‐methylthiouracil and 4‐methylthiothymine were condensed in the presence of TMS triflate with methyl 2,3‐dideoxy‐3‐fluoro‐5‐O‐(4‐phenylbenzoyl)‐D‐erythro‐pentofuranoside (3) and methyl 3‐azido‐5‐O‐(tert‐butyldiphenylsilyl)‐2,3‐dideoxy‐D‐erythro‐pentofuroside (8), respectively, to give the corresponding nucleosides which were deprotected. The 3′‐azido nucleoside was reduced with triphenylphosphine to the corresponding 3′‐amino nucleoside. The 3′‐amino nucleoside was also obtained by condensation of 4‐methylthiothymidine with a 3‐phthalimido sugar 14 followed by deprotection. The 4‐methylthio analogue 11 of AZT showed moderate activity against HIV.
Peroxidase‐catalysed oxidation of different dibenzazepine derivatives
Authors: Liégeois Jean‐Francois , Rogister Francoise , Delarge Jacques , Pincemail Joël 
Published: October 2006

AbstractAccording to a recent hypothesis suggesting the potential role of free radical formation in the clozapine‐induced agranulocytosis, we have evaluated the susceptibility to the peroxidase‐mediated oxidation of different dibenzazepine analogues. On the one hand, compounds with an arylamine group such as clozapine present a high reactivity in the horseradish peroxidase or myeloperoxidase systems and, on the other hand, fluperlapine, though known to induce agranulocytosis, and other debenzothiazepine and dibenzoxazepine derivatives appear insensitive to oxidation. Consequently, among tricyclic derivatives, the way of diaryloxa‐ and diarylthiazepine compounds could be an alternative for the development of safer drugs such as antipsychotics.
Synthesis of Phthalimido‐Desmuramylpeptide Analogues as Potential Immunomodulating Agents
Authors: Urleb Uroš , Krbavčič Aleš , Sollner Marija , Kikelj Danijel , Pečar Slavko 
Published: October 2006

AbstractThe preparation of immunologically active phthalimido desmuramylpeptide analogues 2e‐h, 4c‐d, and 7b is described. The N‐acetylmuramic acid in the muramyl dipeptide has been replaced by a phthaloylated acyclic moiety such as N‐phthaloylated amino acids 1a–c, 2‐(2‐phthalimidoethoxy)acetic acid 3, or by the carbocyclic rac. trans‐2‐(2′‐phthalimidocyclohexyloxy)acetic acid 6.
Synthesis of Some Thiazolo[3,2‐b]‐1,2,4‐triazole‐5(6H)‐ones as Potential Platelet Aggregation Inhibitors
Authors: Tozkoparan Birsen , Akgün Hülya , Ertan Mevlüt , Rübsemann Klaus 
Published: October 2006

AbstractTwenty new compounds having 2‐methyl‐6‐benzylidenethiazolo[3,2‐b]‐1,2,4‐triazole‐5(6H)‐one (2a–d) and 2‐methyl‐6‐(α‐aminobenzyl)thiazolo‐[3,2‐b]‐1,2,4‐triazole‐5‐ol (5–20) structures were synthesized. Their structures were confirmed by elemental and spectroscopic analysis and their platelet aggregation inhibitory activities were investigated.
Struktur‐Wirkungs‐Beziehungen an Isochromanylpenicillinen
Authors: Unterhalt Bernard , Nocon Birgit 
Published: October 2006

AbstractDer Isochromanring wird substituiert und in 1‐Position direkt oder über einen Spacer an 6‐Aminopenicillansäure gebunden. Zusätzlich werden zwei Homoisochromane in die Untersuchung eingebezogen. Die Wirkung der neuen Penicilline wird im grampositiven und gramnegativen Bereich der des Benzylpenicillins gegenübergestellt.
Cytotoxicity and Antimicrobial Activity of Some Naphthol Derivatives
Authors: Shen Ai Yu , Hwang Mei Han , Roffler Steve , Chen Chia Fu 
Published: October 2006

Abstract2‐Hydroxymethyl‐1‐naphthol diacetate (TAC) and sixteen Mannich base derivatives of naphthol were prepared and examined for cytotoxicity and antimicrobial activity. Cytotoxicity was examined against four human carcinoma cell lines. Several derivatives were effective at concentrations < 4 μg/ml. TAC showed the highest cytotoxicity. Inhibition of DNA‐, RNA‐, and protein synthesis by TAC was also studied and discussed. TAC also exhibits potent antimicrobial activity against Enterobacter clocae 23355, Klebsiella pneumonia 13883, Proteus vulgaris 13315, Pseudomonas aeruginosa 27853, Candida parapsilosis, Candida tropicalis, Trichosposon beigelli, and Rhodotorul spp. with minimum inhibitory concentrations of 0.1 ∼ 0.4 μM. These results indicate that esterification by Bruson reaction of 1‐naphthol Mannich base to TAC enhances the cytotoxicity and antimicrobial activity.
A New Rapid and Sensitive High‐Performance Liquid Chromatographic Assay for Diclofenac in Human Plasma
Authors: Hanses Antje , Spahn‐Langguth Hildegard , Mutschler Ernst 
Published: October 2006

AbstractA new rapid and sensitive reversed‐phase HPLC method for the routine analysis of diclofenac in human plasma is described. The method shows high selectivity, sensitivity, and reproducibility employing 4′‐methoxydiclofenac as internal standard (IS) with UV‐detection at 282 nm. The correlation of peak area ratios (diclofenac/IS) versus diclofenac plasma concentrations are linear between 5.0—2000 ng/ml with a detection limit of 3 ng/ml. Intra‐ and interday precision studies yielded coefficients of variation < 6.2 % for all concentrations (range 20.0—1600 ng/ml). The method was applied for the assay of diclofenac in plasma of healthy volunteers after p.o. and rectal dosage of 50 mg diclofenac sodium and was found to be highly suitable for routine analyses.
A Facile and Regioselective Synthesis of Donor‐Substituted 2‐(2‐Halophenyl)acetaldehyde Acetals
Authors: Wünsch Bernhard , Nerdinger Sven 
Published: October 2006

AbstractStarting from vanillin (5a) a facile and high yielding procedure for the preparation of the donor substituted (2‐bromophenyl)‐ and (2‐iodophenyl)acetaldehyde acetals13cand16cis described. Homologization ofO‐benzylvanillin to obtain the phenylacetaldehyde acetal15csucceeds byWittigreaction with the phosphonium chloride11and subsequent addition of methanol.15cis brominated with pyridinium bromide perbromide in methanol to yield the bromo acetal13cin 65 % yield from vanillin. Iodination of15cwith iodine and iodic acid leads to the iodo acetal16c.
Pyridazines, LXXII: On the Synthesis of Azinium and Diazinium Compounds Structurally Related to Pyridazomycin
Authors: Easmon Johnny , Heinisch Gottfried , Holzer Wolfgang , Matuszczak Barbara 
Published: October 2006

AbstractPreparation of series of pyridine‐, pyridazine‐, and pyrazine‐derived carboxamides bearing at the ring N‐atom an alkyl side‐chain with a terminal carboxylic group (7–11) or with a terminal acetylamino malonic ester moiety (13–17, 19–23) is described. Two desaza‐pyridazomycin derivatives (24, 26) and homologs thereof (25, 27) were synthesised. The novel compounds which are structurally related to the antifungal antibiotic pyridazomycin were screened for antifungal activity: preliminary in vitro tests showed no activity.
Synthesis and Dopamine Receptor Binding of 3‐Phenylazepino[5,4,3‐c,d]indole Derivatives
Authors: Gmeiner Peter , Sommer Josef , Höfner Georg 
Published: October 2006

AbstractThe 3‐phenylazepino[5,4,3‐c,d]indole derivatives 5 and 9–11, representing heterocyclic analogs of the selective dopamine D‐1 receptor ligands of the 3‐phenylbenzazepine class, were synthesized starting from the indole‐4‐carboxylate 7. Receptor binding studies employing bovine striatal membranes demonstrated that the test compounds 5, 10, and 11 are able to displace the D‐1 selective radioligand [3H]‐SCH 23390 as well as the D‐2 antagonist [3H]‐spiperone. Compound 5b turned out to be the most potent and selective ligand (ki = 1.8 μM for D‐1 and ki = 8.9 μM for D‐2). It is assumed that the moderate selectivity of 5b is due to the conformational inequality of the 7‐membered rings when compared to the benzazepines. This results in a spatial arrangement of the phenyl substituent which is not able to interact with a ‘subtype selectivity‐inducing site’.
Determination of the in vitro Dissolution Profiles of Ursodeoxycholic Acid Preparations by HPLC with On‐Line Sample Handling
Authors: Scalia S. , Giunchedi P. , Conte U. , Pazzi P. 
Published: October 2006

AbstractA high‐performance liquid chromatographic (HPLC) technique with on‐line sample preparation was developed for monitoring the in vitro dissolution profiles of ursodeoxycholic acid (UDCA) formulations. Since UDCA lacks a strong chromophore, conventional UV determination of the dissolved drug is precluded. The proposed method involves direct injection of large volumes (1–2 ml) of the filtered dissolution medium onto a precolumn dry‐packed with large particulate (40–60 μm octadecylsilica and inserted at the loop position of the HPLC injector. After flushing the precolumn with water, the retained UDCA is transferred by the mobile phase onto the analytical column for analysis. The method is reproducible and rapid, minimizing sample manipulations. The dissolution profiles of different UDCA/polymer preparations in USP simulated gastric and intestinal fluid were determined by on‐line pre‐column purification and preconcentration and reversed‐phase HPLC.Key words: ursodeoxycholic acid; dissolution testing; excipient interference; on‐line sample processing; high‐performance liquid chromatography.
Heterolignanolides: Antitumor Activity of Furyl‐, Thienyl‐, and Pyridyl Analogs of Lignanolides
Authors: Medarde Manuel , de Clairac Rafael PeléEz‐Lamamié , Toém Fernando , López Jose Luis , Feliciano Arturo San , Grávalos Dolores Ga 
Published: October 2006

AbstractA new class of heteroaromatic analogs of lignans, called heterolignanolides, have been tested against several tumor cell lines. These compounds carry diverse heterocyclic rings, instead of the trimethoxyphenyl ring found in the natural lignans yatein and podorhizol. They have moderate antineoplastic activity (P‐388, A‐549, HT‐29) compared with that of yatein. None of the tested compounds has discernible antiviral (HSV‐1, VSV) or enzyme inhibitor (ADA, DHFR, GST) activity.
Platelet Antiaggregant Methoxyphenylthienyl Ketoxime Ethers: Synthesis and Structure‐Activity Relationships
Authors: Varache‐Lembège Martine , Nuhrich Alain , Renard Pierre , Duboudin Françoise , Vercauteren Joseph , Devaux Guy 
Published: October 2006

AbstractSome new oximinoalkanoic (n = 2,3,4) esters and acids derived from methoxyphenylthienyl ketones have been synthesized and evaluated in vitro for their inhibitory effects on arachidonic acid‐induced human platelet aggregation. Of the eighteen oximinoethers tested the most active derivatives, which were four times more active as aspirin, belonged to the para methoxy series with Z configuration and n = 2 or 3.
Synthesis of 1,2,5(6)‐Trisubstituted Benzimidazoles and Evaluation of Their Antimicrobial Activities
Authors: Göker Hakan , Kus Canan , Abbasoglu Ufuk 
Published: October 2006

AbstractA series of 22 benzimidazoles, having several substituents on the azole and benzene nuclei, were prepared and evaluated in vitro for antimicrobial activity. At first 2‐chloro or 2‐chloromethyl‐5(6)‐substituted‐1H‐benzimidazoles were synthesized, which were then substituted at C‐2 with several piperazine or piperidine derivatives. The antibacterial activity of these compounds against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa, and the antifungal activity against Candida albicans, Candida stellatoidea, Candida parapsilosis, and Candida pseudotropicalis were determined as the MIC values. Since compound 12 exhibits good activity, in order to clarify the effect of substituents at C‐1 on the activity, benzimidazole derivatives having ethyl, allyl, benzyl, and p‐fluorobenzyl substituents at C‐1 were prepared, and slightly increased activity was seen.
Pyrazoles as Potential Histamine H3‐Receptor Antagonists
Authors: Kieć‐Kononowicz Katarzyna , Ligneau Xavier , Schwartz Jean‐Charles , Schunack Walter 
Published: October 2006

AbstractIn search of structure‐activity relationships among histamine H3‐receptor antagonists, the imidazole ring of known H3‐receptor antagonists was replaced by different heteroaromatic ring systems. Thus, pyrazoles with ether (4,5) and carbamate (6,7) moieties as functional groups were synthesized. Reaction of the hydrochloride of 4‐(3‐hydroxypropyl)pyrazole (1) with phenyl or benzyl isocyanates mainly gave the carbamates 6 and 7, whereas a similar reaction with 1 as the free base furnished the N‐carbamoylpyrazoles 8 and 9. The bifunctional pyrazoles 10 and 11 were formed as by‐products. The compounds obtained did not show significant H3‐receptor antagonist activity in vitro (rat brain cortex) or in vivo (mouse brain). These results demonstrate the importance of the imidazole moiety for H3‐receptor antagonists. The new compounds were also screened for H1‐receptor antagonist activity on the isolated guinea‐pig ileum and for H2‐receptor antagonist activity on the isolated spontaneously beating guinea‐pig right atrium. The substances showed only weak antagonistic activity at both histamine receptors H1 and H2.
Tricyclic CNS Active Agents by Intramolecular Oxa‐Pictet‐Spengler Reaction
Authors: Wünsch Bernhard , Zott Matthias , Höfner Georg , Bauschke Gerd 
Published: October 2006

AbstractMitsunobu inversion of the (S)‐configurated lactate (S)‐7, which is prepared in four steps starting form (S)‐tyrosine, leads to the (R)‐configurated lactate (R)‐7. The key step in the transformation of the enantiomeric lactates (S)‐7 and (R)‐7 into the benzomorphan analogous tricycles (R,S)‐16a,b, (S,R)‐16a,b, (S,S)‐22, and (R,R)‐22 is an intramolecular Oxa‐Pictet‐Spengler reaction: The amides (S)‐13, (R)‐13, (S)‐19 and (R)‐19, in which the carbonyl moiety — masked as an acetal — is linked to the 2‐phenylethanol moiety, are cyclized to give the tricyclic amides (R,S)‐15, (S,R)‐15, (S,S)‐21, and (R,R)‐21, respectively. In a concentration of 100 μM both enantiomers of 16a, 16b, and 22 are not able to compete with 3H‐(+)‐MK 801 for the phencyclidine binding sites of NMDA receptors. In vivo, only (R,S)‐16b and (S,S)‐22 exhibit weak sedative and analgesic activity.
Resolution, EPC‐Syntheses, Absolute Stereochemistry, and Pharmacology of the (S)‐(+)‐ and (R)‐(—)‐Isomers of the MAO‐A Inhibitor Tetrindole Hydrochloride
Authors: Bös Michael , Canesso Rolf , Kettler Rolf , Keller Hans H. , Schönholzer Peter 
Published: October 2006

AbstractResolution of (RS)‐tetrindole (3) and enantioselective reductions of the imine 7 yielded (S)‐(+)‐(4) and (R)‐(−)‐tetrindole (5). The absolute stereochemistry of 4 was established by X‐ray analysis of the corresponding Mosher amide 6. From in vitro as well as in vivo data (MAO‐inhibiton, levels of monoamines and their respective metabolites in rat brain), 4 was identified as the eutomer.
Quality Control of Peptide Drugs. Chiral Amino Acid Analysis versus Standard for Icatibant Acetate
Authors: Ermer Joachim , Gerhardt Jürgen , Siewert Martin 
Published: October 2006

AbstractA method of chiral amino acid analysis versus standard is presented. By treating the peptide sample and a chiral standard whose intrinsic chiral composition is known in the same way, i.e. simultaneous hydrolysation and analysis, exact corrections can be made for the sequence‐related and many hydrolysation‐related racemisations. The accuracy obtained in this way permits use of the results for quality control of the chiral purity of peptide drugs. Using the bradykinin antagonist Icatibant acetate (INNM) the method was validated with respect to its precision, accuracy, specificity, limit of detection, and robustness.
Synthesis and Authentication of Iodoazidophenpyramine, a Photoaffinity Reporter Ligand Previously used for Histamine H1‐Receptor Labelling
Authors: Sorba Giovanni , Tertiuk Wasyl , Ganellin C. Robin 
Published: October 2006

AbstractThe synthesis is described of aminophenpyramine (7) (N‐{5‐[2‐(4‐aminophenyl)ethananmido]pentanyl}‐N′‐(4‐methoxybenzyl)‐N‐methyl‐N′‐(2‐pyridinyl)‐1,2‐ethandiamine), its monoiodo‐ and diiodo‐derivatives (8 and 9), and iodoazidophenpyramine (1). The last compound is synthesised by two different routes to confirm the identity of the [125I]iodinated ligand previously made only in solution and used for characterisation of the histamine H1‐receptor protein. The procedures employ the novel intermediates 4‐amino‐3‐iodo‐phenylacetic acid (11) and 4‐azido‐3‐iodo‐phenylacetic acid (13). They have general applicability to the synthesis of non‐radioactive iodinated photoaffinity receptor ligands which may be required for chemical authentication of the corresponding radiolabelled compounds.