bluuebunny/crossref_metadata_2025 huggingface dataset:
Synthesis and Non-Aqueous Medium Titrations of Some New 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives
Authors: Yüksek Haydar , Ücüncü Osman , Alkan Muzaffer , Ocak Zafer , Bahceci Sule
Published: October 2008

The synthesis of 3-alkyl(aryl)-4-(3-ethoxy-4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones 3 from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones 2 with 3-ethoxy-4-hydroxybenzaldehyde is described.The acetylation and methylation reactions of the compounds 3 giving compounds of type4 and 5, respectively, were investigated. The newly synthesized compounds werecharacterized using elemental analyses and IR, 1H-NMR, 13C-NMR and UV spectral data.In addition, to investigate the effects of solvents and molecular structure upon acidity,compounds 3 were titrated potentiometrically with tetrabutylammonium hydroxide infour non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, acetonitrile and N,N-dimethylformamide). The half-neutralization potential values and the corresponding pKavalues were determined for all cases.
Terpenoids from Cleome droserifolia (Forssk.) Del
Authors: El-Askary Hesham   I.
Published: October 2008

A new diacetyl triterpene lactone, drosericarpone (2), was isolated from the hexane extract of the herb Cleome droserifolia, together with buchariol (1, a sesquiterpene oxide, isolated for the first time from Cleome species) and stigmasterol glucoside (3). The structures of 1-3 were identified by spectroscopic means.
Synthesis and Characterization of Nitro-p-xylenes
Authors: Yan-Hong L. , Tong-Lai Z. , Jian-Guo Z. , Jin-Yu G. , Kai-Bei Y.
Published: October 2008

In this paper we elected to nitrate p-xylene because this compound has onlyone mononitro- and trinitro- isomer. Trinitro-p-xylene was used as a starting material forthe synthesis of other compounds in subsequent work. The mononitration of p-xylene canbe easily carried out at 30°C. Nitro-p-xylene is easily nitrated to dinitro-p-xylene at atemperature of 80°C. The trinitro-p-xylene can be obtained at 120°C. Single crystals of2,3-dinitro-p-xylene and 2,3,5-trinitro-p-xylene were grown using theslow cooling method and we report the X-ray structure of the former. The thermaldecomposition of the compounds was studied using differential scanning calorimetry(DSC) and thermogravimetry-derivative thermogravimetry (TG-DTG) techniques andFT-IR. The target compounds were also characterized by 1H-NMR, 13C-NMR and MS.
Synthesis of 4'-(2,6,6-Trimethyl -2-Cyclohexen-1-yl) -3'-Buten-2'-Ketoxime-N-O-Alkyl Ethers
Authors: Banerjee T. , Dureja P.
Published: October 2008

4'-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3'-buten-2'-ketoxime-N-O-alkyl ethershave been synthesized starting from α-ionone, separated into their E and Z isomers andcharacterized on the basis of 1H-NMR and mass spectra.
The Syntheses of Some Novel (Naphthalen-1-yl-selenyl)acetic Acid Derivatives
Authors: Yavuz Serkan , Dişli Ali , Yıldırır Yılmaz , Türker Lemi
Published: October 2008

Some new (naphthalen-1-yl-selenyl)acetic acids derivatives 7a-d have been synthesized by two different methods, using naphthylselenols or naphthylselenocyanates. The structures of the products were investigated by spectroscopic methods.
Microbial Hydroxylation of Sclareol by Rhizopus Stolonifer
Authors: Díez D. , Sanchez J.  M. , Rodilla J.  M. , Rocha P.  M. , Mendes R.  S. , Paulino C. , Marcos I.  S. , Basabe P. , Urones J. G.
Published: October 2008

Incubation of sclareol with Rhizopus stolonifer affords in high yield a mixture of triols with 18-hydroxy-sclareol as the main component.
Preparation of an Eight-Membered Sesquiterpene Lactone Resulting from Sequential Gif System GoAggIII and MCPBA Oxidation of ( )-10β,14-Dihydroxy-allo-aromadendrane
Authors: De Bodas M. , Marques M. , Beatriz A. , De Lima D.
Published: October 2008

Studies aimed at a comparison of chemical, biomimetic (Gif system GoAggIII)and enzymatic (CHMO) transformations of natural ( )-10β,14-dihydroxy-allo-aromadendrane have led to preparation of an eight-member sesquiterpene lactone.
Improved Synthesis of β-D-6-Methylpurine Riboside and Antitumor Effects of the β-D- and α-D-Anomers
Authors: Marasco C. , Pera P. , Spiess A. , Bernacki R. , Sufrin J.
Published: October 2008

6-Methylpurine-β-D-riboside (β-D-MPR) has been synthesized by coupling6-methylpurine and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose using conditions that producethe β-D-anomer exclusively. The in vitro antitumor effects of β-D-MPR and 6-methyl-purine-α-D-riboside (α-D-MPR) in five human tumor cell lines showed that β-D-MPR washighly active (IC50 values ranging from 6 to 34 nM). α-D-MPR, although less active than β-D-MPR, also exhibited significant antitumor effects (IC50 values ranging from 1.47 to 4.83"µ"M).
Special Issue: Selected Papers from the 2nd International Conference on Natural Products and Physiologically Active Substances (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry” (EAHM-2004)
Authors: Babaev Eugene , Tkachev Alexey
Published: October 2008

Two meetings, ICNPAS-2004 and EAHM-2004, were jointly held on September 12-17, 2004 in Novosibirsk, Russia.[...]
Organic Synthesis in Pheromone Science
Authors: Mori Kenji
Published: October 2008

Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones are summarized to emphasize biodiversity as revealed in pheromone perception.
The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates
Authors: Gautier A. , Lopin C. , Garipova G. , Dubert O. , Kalinina I. , Salcedo C. , Balieu S. , Glatigny S. , Valnot J. , Gouhier G. , Piettre S.
Published: October 2008

Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the addition of phosphorus-centered radicals onto gem–difluoroalkenes or on a process involving the addition of lithiodifluorophosphono- thioates 91 onto a ketone and the subsequent deoxygenation reaction of the adduct. The radical route successfully developed a practical route to α,α–difluoro–H–phosphinates which proved to be useful intermediates to a variety of phosphate isosters. The ionic route led to the first preparation of phosphonodifluoromethyl analogues of nucleoside– 3’–phosphates.
An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation
Authors: Kuznetsov Alexey G. , Bush Alexander A. , Rybakov Viktor B. , Babaev Eugene V.
Published: October 2008

Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2- phenylindolizine was confirmed by X-Ray analysis. The reactivity of the 5-CHO- and 5- COPh groups toward some nucleophiles has been examined, and some additional classes of derivatives (oximes and alcohols) have been obtained. The possibility of Suzuki cross- coupling of 5-iodoindolizines and boronic acids was proven.
Studies Towards the Total Synthesis of Di- and Sesterterpenes with Dicyclopenta[a,d]cyclooctane Skeletons. Three-component Approach to the A/B Rings Building Block
Authors: Michalak K. , Michalak M. , Wicha J.
Published: October 2008

Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents was constructed using as key steps ring closing metathesis reaction and Wagner - Meerwein rearrangement. Ring closing metathesis reaction leading to cyclopenta[8]annulene was studied in detail.
The tert-Amino Effect in Heterocyclic Chemistry. Synthesis of Spiro Heterocycles
Authors: D’yachenko E. , Glukhareva T. , Dyudya L. , Eltsov O. , Morzherin Y.
Published: October 2008

The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the “tert-amino effect” could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good yields in a one-pot reaction.
Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
Authors: Kazhkenov Zeinul-Gabiden M. , Bush Alexander A. , Babaev Eugene V.
Published: October 2008

A series of previously unavailable derivatives of 2-alkyl- and 2-benzylderivatives of oxazolo[3,2-a]pyridines III were obtained via tandem ring opening and ring closure from stable mesoionic 3-acyloxazolo[3,2-a]pyridinium-2-olates I. The key intermediates of this tandem transformation are N-(b-oxoethyl)pyridones-2 II obtained by Dakin-West acylation of (pyridone-2-yl-1)acetic acid. An example of further utilization of this strategy is illustrated by preparation of unknown 2-benzylimidazo[1,2-a]pyridine from the salt I and ammonia.
A Facile Synthesis of Novel Herbicidal 1-Phenyl-piperazine-2,6-diones
Authors: Li B. , Xiang D. , Hsu C. , Liu Z. , Wu C. , Yang H.
Published: October 2008

Novel 1-phenyl-piperazine-2,6-diones were prepared by a new facile synthetic routeusing methyl N-substituted iminomonoacetate as starting material. The structures of thesecompounds were established by 1H-NMR, 13C-NMR and GC/MS. 2-(4-Chloro-5-cyclo-pentyl-oxy-2-fluorophenyl)-tetrahydro-2H-pyrido-[1,2-a]-pyrazine-1,3-(4H,6H)-dione displayed thegreatest herbicidal activity.
New Multi-1,2,3-Selenadiazole Aromatic Derivatives
Authors: Al-Smadi M. , Ratrout S.
Published: October 2008

The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy- acetophenone to give compounds 3a-d which are transformed through the reaction with semicarbazide hydrochloride or ethyl hydrazine carboxylate into the corresponding semicarbazones derivatives 4a-d or hydrazones 5a-d. The reaction with selenium dioxide leads to regiospecific ring closure of semicarbazones or hydrazones to give the multi- 1,2,3-selenadiazole aromatic derivatives in high yield.
Poly[3-(3,4-dihydroxyphenyl)glyceric Acid], A New Biologically Active Polymer from Symphytum Asperum Lepech. and S.Caucasicum Bieb. (Boraginaceae)
Authors: Barbakadze V. , Kemertelidze E. , Targamadze I. , Mulkijanyan K. , Shashkov A. , Usov A.
Published: October 2008

Two high-molecular water-soluble preparations with high anticomplementary, antioxidant, antilipoperoxidant and antiinflammatory activities were isolated from the roots of Symphytum asperum and S. caucasicum. Their main chemical constituent was found to be poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], according to IR and NMR spectroscopy. The Symphytum high-molecular preparations can modulate in vitro B- chronic lymphocytic leukaemia (B-CLL) cells apoptosis and cell cycle progression.
Oxidative Stress, Lipid Profile and Liver Functions in Average Egyptian Long Term Depo Medroxy Progesterone Acetate (DMPA) Users
Authors: Faddah L. , Al-Rehany M. , Abdel-Hamid N. , Bakeet A.
Published: October 2008

Depo-medroxy progesterone acetate (DMPA, Depo-Provera®) is used in morethan 80 countries as a long-acting contraceptive administered as a single intramuscular(i.m) injection of 150 mg/3 months. The present study was set up to investigate theeffects of DMPA on 80 average Egyptian women classified into four groups comprisingthose using the drug for one, two, three and four years, respectively, compared to acontrol group (N = 20) of married non-hormonally – treated women of similar ages. Thedrug showed a transient significant elevation of alanine aminotransferase activity (ALT)without an apparent effect on other liver indices, namely total bilirubin (T.Bil) level,aspartate aminotransferase (AST) and alkaline phosphatase (ALP) activities. Only thelow density/high density lipoproteins cholesterol ratio (LDLC/HDLC) was gradually andnon-significantly (ns) increased in comparison to control group, however, neither totalcholesterol (TC) nor triglycerides (TG) were affected by the drug. The lipid peroxideproduct malondialdehyde (MDA) was significantly elevated in an gradual manner with acorresponding decrease in reduced glutathione (GSH), without any change in blood nitricoxide (NO) levels. It can be concluded that DMPA may be considered as a safecontraceptive medication for the studied group of women, but that special care should beexercised for cardiovascular, hepatic and other patients more sensitive to the harmfuleffects of free radicals. Alternatively, supportive medications are advisable for eachexposed case to secure against the possible irreversible adverse effects of the drug by continuous use. In addition, annual re-evaluation is much more advisable despite the proven safety of the drug.
Synthesis of Thiadiazoles and 1,2,4-Triazoles Derived from Cyclopropane Dicarboxylic Acid
Authors: Sharba A. , Al-Bayati R. , Rezki N. , Aouad M.
Published: October 2008

New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane (7) by ring closure in an alkaline medium. The thiadiazole 2 and the triazole 7 were converted into a variety of derivatives.
Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene
Authors: Sharba A. , Al-Bayati R. , Aouad M. , Rezki N.
Published: October 2008

In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the N-formyl acid hydrazide 4, which upon refluxing with phosphorous pentoxide or phosphorous pentasulphide in xylene yielded the corresponding 2- (3-chloro-1-benzothien-2-yl)-1,3,4-oxadiazole (5) and 2-(3-chloro-1-benzo-thien-2-yl)-1,3,4- thiadiazole (6). Reaction of 1-thiosemicarbazide 7 with NaOH leads to ring closure giving 5- (3-chloro-1-benzothien-2- yl)-4H–triazole-3-thiol (8) which is converted into a number of derivatives 9-12 Reaction of 2 with phenyl isothiocyanate and NaOH afforded 5-(3-chloro- 1-benzothien-2-yl)-4-(phenyl)-4H-1,2,4-triazole-3-thiol (14).
Synthesis of Hydroxy Sulfonate Surfactants
Authors: Rist O. , Carlsen P.
Published: October 2008

The selective synthesis of sulfonate surfactants with side chains containing ether- and hydroxy groups was carried out using cyclic sulfates as epoxide analogues. The main chain was elaborated from 1,2-dodecane sulfate by the addition of various hydroxy/alkoxysulfonates. Ethyleneoxy- and 1,2-propyleneoxy- groups were introduced using ethylene sulfate and 1,2-propylene sulfate, respectively.
HPLC Analysis of Aliphatic Sulfonate Surfactants using Ion-Pair Detection
Authors: Zahrobsky M. , Camporese D. , Rist O. , Carlsen P.
Published: October 2008

A method was developed for the analysis of a number of surfactants which contained no UV-chromophores, using RP-HPLC with Indirect Photometric Detection, IPD. Pyridinium salts such as N-methylpyridinium iodide, N-methyl-2,2'-dipyridinium iodide and N,N'-dimethyl-2,2'-dipyridinium diiodide, were used as the visualization reagents, forming ion-pair complexes with the sulfonate surfactants. This allowed ordinary UV-detection. N-methylpyridinium iodide proved to be a suitable reagent, both with respect to ease of preparation and response. The eluents consisted of mixtures of acetonitrile and water, being 0.1 - 0.25 mM with respect to pyridinium salt. The method was sensitive and exhibited good signal to noise ratios, as well as linear responses over a wide concentration range. All of the analyzed surfactants were separated, including the diastereomeric forms of some of the surfactants.
Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
Authors: Fernandez L. , Santo M. , Reta M. , Giacomelli L. , Cattana R. , Silber J. , Risso M. , Cerecetto H. , Gonzalez M. , Olea-Azar C.
Published: October 2008

The relationship between the herbicidal activity of a number of novel 1,2,5-oxadiazole N-oxides and some physicochemical properties potentially related with thisbioactivity, such as polarity, molecular volume, proton acceptor ability, lipophilicity, andreduction potential were studied. The semiempirical molecular orbital method AM1 wasused to calculate theoretical descriptors such as dipolar moment, molecular volume,Mulliken ́s charge and the octanol/water partition coefficients (log Po/w). The values ofthe reduction potentials (Er) were obtained by cyclic voltammetry. In addition, theretention factors (log k’w) on a reversed-phase high-performance liquid chromatography(RP-HPLC) column in pure aqueous mobile phases were measured for several N-oxidederivatives. The log k’w values show good correlation with the calculated values of logPo/w, showing that the chromatographic parameter can be used as lipophilicity descriptorfor these compounds. The multiple regression analysis between the descriptors for the N-oxide derivatives and the herbicide activity indicate that the variance in the biologicalactivity can be explained by changes in the lipophilicity and in the reduction potential.
Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate
Authors: Tulyasheva M. , Rasulev B. , Tojiboev A. , Turgunov K. , Tashkhodjaev B. , Abdullaev N. , Shakhidoyatov K
Published: October 2008

The new compounds (Z)-ethyl 2-cyano-2-(3H- and 2-methyl-3H-quinazoline-4-ylidene) acetate (1 and 2, respectively) were synthesized by multi-step reactions. Thestructures in a solution have been determined by 1H-NMR spectroscopy and in the crystalform by X-ray analysis. Molecule 1 crystallized in a primitive monoclinic cell, spacegroup Р21/c. The cell dimensions are a=7.970(6) å, b=7.061(2) å, c=20.537(7) å,β=97.69(5)°, V=1145.3(10) å3. Molecule 2 crystallized in a triclinic cell, space group P-1, the cell dimensions are a=8.196(5) å, b=8.997(6) å, c=9.435(4) å, α=74.22(4)°,β=89.75(4)°, γ=74.07(5)°, V=641.9(6) å3. In both compounds the presence of intra-molecular NH---O=C hydrogen bonding between the nitrogen atom in position 3 of thequinazoline ring and a carbonyl group of the ethyl cyanoacetate residue was proven byquantum-chemical, 1H-NMR and X-ray methods.
Synthesis and Biological Activity of Novel Amino Acid-(N'-Benzoyl) Hydrazide and Amino Acid-(N'-Nicotinoyl) Hydrazide Derivatives
Authors: Khattab Sherine N.
Published: October 2008

The coupling reaction of benzoic acid and nicotinic acid hydrazides with N- protected L-amino acids including valine, leucine, phenylalanine, glutamic acid and tyrosine is reported. The target compounds, N-Boc-amino acid-(N`-benzoyl)- and N- Boc-amino acid-(N`-nicotinoyl) hydrazides 5a-5e and 6a-6e were prepared in very high yields and purity using N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl- methylene]-N-methyl-methanaminium hexafluorophosphate N-oxide (HATU) as coupling reagent. The antimicrobial activity of the Cu and Cd complexes of the designed compounds was tested. The products were deprotected affording the corresponding amino acid-(N`-benzoyl) hydrazide hydrochloride salts (7a-7e) and amino acid-(N`- nicotinoyl) hydrazide hydrochloride salts (8a-8e). These compounds and their Cu and Cd complexes were also tested for their antimicrobial activity. Several compounds showed comparable activity to that of ampicillin against S. aureus and E. coli.
A Good Yield and a High Standard
Authors: Lin Shu-Kun
Published: October 2008

The new journal Molecules publishes peer-reviewed research papers on synthetic chemistry and natural product chemistry.[...]
2004 RACI One-day Natural Products Group Symposium
Authors: Karuso P.
Published: October 2008

This special issue of Molecules is dedicated to the Royal Australian Chemical Institute’s Natural Products group.[...]
25 Years of Natural Product R&D with New South Wales Agriculture
Authors: Southwell I.
Published: October 2008

Following recent NSW Government restructuring, the Department of Agriculture now exists in a composite form along with Forestry, Fisheries and Minerals in the new NSW Department of Primary Industries. This paper outlines some of the highlights of secondary metabolite R&D accomplished in the 25 years since the essential oil research unit was transferred from the Museum of Applied Arts & Sciences, Sydney to NSW Agriculture’s Wollongbar Agricultural Institute on the NSW north coast. The essential oil survey was continued, typing the Australian flora as a suitable source of isolates such as myrtenal (Astartea), myrtenol (Agonis), methyl chavicol (Ochrosperma), α-phellandren-8-ol (Prostanthera), methyl myrtenate (Darwinia), methyl geranate (Darwinia), kessane (Acacia), cis-dihydroagarofuran (Prosthanthera), protoanemonin (Clematis), isoamyl isovalerate (Micromyrtus), methyl cinnamate (Eucalyptus) and bornyl acetate (Boronia). Many of these components are used, or have potential use in the fragrance, flavour, medicinal plant or insect attraction fields. Two weeds toxic to livestock in the Central West of the State are also harvested commercially as medicinal plants. Measurement of hypericin concentrations in the various plant parts of St John’s Wort (Hypericum perforatum) over two seasons has shown that the weed can be effectively managed by grazing sheep during the winter months when toxin levels are low. Syntheses of β-carbolines tribulusterine and perlolyrine have shown that the former alkaloid was misidentified in the literature and hence not the toxic principle responsible for Tribulus staggers in sheep. Poor quality (high 1,8-cineole – low terpinen-4-ol) oil bearing tea tree (Melaleuca alternifolia) plantations have been established to the detriment of many a tea tree farmer. Analytical methods developed to check leaf quality at an early age indicated precursor sabinene constituents that convert to the active terpinen-4-ol both as the leaf matures or as the precursors are distilled for oil production. Tea tree’s major insect pest, pyrgo beetle (Paropsisterna tigrina), was seen to selectively metabolize only 1,8-cineole from it’s monoterpenoid-rich diet. Characterization of these and other metabolites from myrtaceous herbivores showed a species specific production of predominately ring hydroxylated products, some of which were attractive when bioassayed against adult beetles.
Bioavailability of Echinacea Constituents: Caco-2 Monolayers and Pharmacokinetics of the Alkylamides and Caffeic Acid Conjugates
Authors: Matthias A. , Penman K. , Matovic N. , Bone K. , De Voss J. , Lehmann R.
Published: October 2008

Many studies have been done over the years to assess the effectiveness of Echinacea as an immunomodulator. We have assessed the potential bioavailability of alkyl- amides and caffeic acid conjugates using Caco-2 monolayers and compared it to their actual bioavailability in a Phase I clinical trial. The caffeic acid conjugates permeated poorly through the Caco-2 monolayers. Alkylamides were found to diffuse rapidly through Caco-2 monolayers. Differences in diffusion rates for each alkylamide correlated to structural variations, with saturation and N-terminal methylation contributing to decreases in diffusion rates. Alkylamide diffusion is not affected by the presence of other constituents and the results for a synthetic alkylamide were in line with those for alkylamides found in an ethanolic Echinacea preparation. We examined plasma from healthy volunteers for 12 hours after ingestion of Echinacea tablets manufactured from an ethanolic liquid extract. Caffeic acid conjugates could not be identified in any plasma sample at any time after tablet ingestion. Alkylamides were detected in plasma 20 minutes after tablet ingestion and for each alkylamide, pharmacokinetic profiles were devised. The data are consistent with the dosing regimen of one tablet three times daily and supports their usage as the primary markers for quality Echinacea preparations.
An Ethnopharmacological Study of Medicinal Plants in New South Wales
Authors: Brouwer N. , Liu Q. , Harrington D. , Kohen J. , Vemulpad S. , Jamie J. , Randall M. , Randall D.
Published: October 2008

The Australian Aboriginal people have used plants as medicine and food for thousands of years, however, this traditional knowledge is documented only to a limited extent, and is in danger of being lost. The Indigenous Bioresources Research Group (IBRG) aims to help Australian Aboriginal communities to preserve their customary medicinal knowledge, and to provide information that can be used for their cultural or educational purposes, as well as for scientific advancement. This work is undertaken in close collaboration with Australian Aboriginal communities in New South Wales. The project is multidisciplinary, combining an ethnobotanical and an ethnopharmacological approach, which includes biological and chemical investigations, as well as developing best practices for protecting traditional knowledge. This paper describes the general strategy of the project as well as methods used in the ethnopharmacological study. Ethnobotanical databases are set up for each participating community. Plant material is collected, extracted, and active compounds are isolated using a bioassay-guided fractionation approach. All extracts and compounds are tested for biological activity in antimicrobial assays (disc diffusion, resazurin, fluorescein diacetate), neurological assays or anti-inflammatory assays, depending on their traditional use.
Theoretical Study of Molecular Determinants Involved in Signal Binding to the TraR Protein of Agrobacterium tumefaciens
Authors: Goh W. , Rice S. , Kumar N.
Published: October 2008

N-acylated homoserine lactone (AHL) mediated cell-cell communication in bacteria is dependent on the recognition of the cognate signal by its receptor. This interaction allows the receptor-ligand complex to act as a transcriptional activator, controlling the expression of a range of bacterial phenotypes, including virulence factor expression and biofilm formation. One approach to determine the key features of signal- binding is to model the intermolecular interactions between the receptor and ligand using computational-based modeling software (LigandFit). In this communication, we have modeled the crystal structure of the AHL receptor protein TraR and its AHL signal N-(3- oxooctanoyl)-homoserine lactone from Agrobacterium tumefaciens and compared it to the previously reported antagonist behaviour of a number of AHL analogues, in an attempt to determine structural constraints for ligand binding. We conclude that (i) a common conformation of the AHL in the hydrophobic and hydrophilic region exists for ligand-binding, (ii) a tail chain length threshold of 8 carbons is most favourable for ligand-binding affinity, (iii) the positive correlation in the docking studies could be used a virtual screening tool.
Towards a Synthesis of Naphthalene Derived Natural Products
Authors: McCulloch M. , Barrow R.
Published: October 2008

Dieckmann-type cyclization reactions have been employed in the synthesis of the alkyl substituted naphthoquinone 11 and the naphthalenes 10 and 12. Various conditions for the benzylic oxidation of these compounds have been investigated with a view towards the synthesis of some naphthalene based natural products.
Modulation of macrophage immune responses by Echinacea
Authors: Stevenson L. , Matthias A. , Banbury L. , Penman K. , Bone K. , Leach D. , Lehmann R.
Published: October 2008

Echinacea preparations are widely used herbal medicines for the prevention and treatment of colds and minor infections. There is little evidence for the individual components in Echinacea that contribute to immune regulatory activity. Activity of an ethanolic Echinacea extract and several constituents, including cichoric acid, have been examined using three in vitro measures of macrophage immune function – NF-κB, TNF- α and nitric oxide (NO). In cultured macrophages, all components except the monoene alkylamide (AA1) decreased lipopolysaccharide (LPS) stimulated NF-κB levels. 0.2 μg/ml cichoric acid and 2.0μg/mL Echinacea Premium Liquid (EPL) and EPL alkylamide fraction (EPL AA) were found to significantly decrease TNF-α production under LPS stimulated conditions in macrophages. In macrophages, only the alkylamide mixture isolated from the ethanolic Echinacea extract decreased LPS stimulated NO production. In this study, the mixture of alkylamides in the Echinacea ethanolic liquid extract did not respond in the same manner in the assays as the individual alkylamides investigated. While cichoric acid has been shown to affect NF-κB, TNF-α and NO levels, it is unlikely to be relevant in the Echinacea alterations of the immune response in vivo due to its non- bioavailability – i.e. no demonstrated absorption across the intestinal barrier and no detectable levels in plasma. These results demonstrate that Echinacea is an effective modulator of macrophage immune responses in vitro.
Isolation and Structure Elucidation of a Novel Yellow Pigment from the Marine Bacterium Pseudoalteromonas tunicata
Authors: Franks A. , Haywood P. , Holmström C. , Egan S. , Kjelleberg S. , Kumar N.
Published: October 2008

The marine environment is a major source for many novel natural compounds. A new yellow pigment has been isolated from the marine bacterium P. tunicata and identified as a new member of the tambjamine class of compounds. The structural identification was achieved by a combination of 1D and 2D-NMR spectroscopy and high resolution mass spectrometry data.
9-Hydroxyfurodysinin-O-ethyl Lactone: A New Sesquiterpene Isolated from the Tropical Marine Sponge Dysidea arenaria
Authors: Piggott A. , Karuso P.
Published: October 2008

A new sesquiterpene, 9-hydroxyfurodysinin-O-ethyl lactone, has been isolated from a New Caledonian Dysidea arenaria, along with three known compounds. The possible incorporation of the ethyl ether from the extraction solvent is discussed.
Pyrazolo[4,3-e][1,2,4]triazines: Purine Analogues with Electronic Absorption in the Visible Region
Authors: Mojzych Mariusz , Rykowski Andrzej , Wierzchowski Jacek
Published: October 2008

Synthesis of several pryrazolo[4,3-e][1,2,4]-triazines is described. Theabsorption spectrum of some 5-substituted derivatives was found to extend to the visibleregion. These compounds were found to inhibit some enzymes of purine metabolism, likexanthine oxidase or bacterial purine-nucleoside phosphorylase with Ki values in the 10-3 –10-5 M range.
Eco-friendly Oxidative Iodination of Various Arenes with Sodium Percarbonate as the Oxidant†
Authors: Zielinska Agnieszka , Skulski Lech
Published: October 2008

Six easy laboratory procedures are presented for the oxidative iodination ofvarious aromatics, mostly arenes, with either molecular iodine or potassium iodide (usedas the sources of iodinating species, I or I3 ), in the presence of sodium percarbonate(SPC), a stable, cheap, easy to handle, and eco-friendly commercial oxidant.
Synthesis of New Potentially Bioactive Bicyclic 2-Pyridones
Authors: Crozet Maxime  D. , George Pascal , Crozet Michel P. , Vanelle Patrice
Published: October 2008

Three convenient methods of reduction of the nitro group of 5-nitroimidazoles and 5-nitrothiazole that bear a diethylmethylene malonate group in an ortho-like position with respect to the nitro group and cyclization of the resulting amino derivatives are reported. These reactions afforded the target bicyclic 2-pyridones in good to excellent yields.
Facile Preparation of Peracetates and Per-3-bromobenzoates of α-Mono- and Disaccharides
Authors: Wang Zerong , Matin Mahfuza , Sheikh Samia
Published: October 2008

A simple and convenient method for the preparation of fully acetylated and (3- bromo)benzoylated α-monosaccharides and disaccharides through vigorous mechanical mixing of solid reactants on a high speed shaker is described. Using this technique a variety of α-acylated sugars are prepared, including penta-O-acetyl-α-D-galactopyranose, penta-O- acetyl-α-D-glucopyranose, penta-O-acetyl-α-D-mannopyranose, octa-O-acetyl-α-lactose, penta-O-(3-bromo)benzoyl-α-D-galactopyranose, penta-O-(3-bromo)benzoyl-α-D-gluco- pyranose, penta-O-(3-bromo)benzoyl-α-D-mannopyranose, and octa-O-(3-bromo)benzoyl- α-lactose.
Diastereoselective Spiroannulation of Phenolic Substrates: Synthesis of (±)-2-tert-Butyl-6-methoxy-1-oxaspiro[4,5]deca-6,9-diene-8-one
Authors: Plourde G. , English N.
Published: October 2008

The synthesis of a new spiroether is described. The title compound is obtained as a diastereomeric mixture in 45% yield.
Formation of New Alkynyl(phenyl)iodonium Salts and Their Use in the Synthesis of Phenylsulfonyl Indenes and Acetylenes
Authors: Koumbis A. , Kyzas C. , Savva A. , Varvoglis A.
Published: October 2008

The preparation of phenylsulfonyl indene derivatives and phenylsulfonyl- acetylenes from readily available alkynyl(phenyl)iodonium tetrafluoroborates and triflates was investigated using phenylsulfinate as nucleophile.
A Novel Synthesis of (E)-3-Methylthio-3-Substituted Arylamino-2-Cyanoacrylates under Microwave Irradiation
Authors: Ouyang Guiping , Song Baoan , Zhang Huiping , Yang Song , Jin Linhong , Li Qianzhu , Hu Deyu
Published: October 2008

A facile synthesis of 3-methylthio-3-arylamino-2-cyanoacrylates from 3,3-dimethylthioacrylate and aromatic amines or amino pyridines has been achieved in moderate to high yields (64.0% ~ 93.5%) in 30 minutes at 50°C under microwave irradiation. This method is very simple and the reaction conditions are mild, environmentally friendly and more importantly, quick. In the 3-(4,5-dimethylthiazol- 2-yl)-2,5-diphenyltetrazolium bromide (MTT) test, some of the title compounds were found to possess good antiproliferation activity towards PC3 cells.
Urea- Hydrogen Peroxide (UHP) Oxidation of Thiols to the Corresponding Disulfides Promoted by Maleic Anhydride as Mediator
Authors: Karami Bahador , Montazerozohori M. , Habibi M. H.
Published: October 2008

Urea-hydrogen peroxide (UHP) was used in the presence of maleic anhydride as mediator in a simple and convenient method for the oxidation in high yield of some thiols to the corresponding disulfides. Peroxymaleic acid formed in situ from the reaction of UHP with maleic anhydride has a key role in this oxidation. Performance of the reaction in various solvents showed that methanol was the solvent of choice at 0 oC. The products were isolated by simple filtration on silica gel.
Alumina and Silica Oxides as Catalysts for the Oxidation of Benzoins to Benzils under Solvent-free Conditions
Authors: Noroozi –Pesyan N. , Dabbagh A.  H.
Published: October 2008

Alumina or silica gel are used as catalysts for a solvent-free oxidation of benzoins to the corresponding benzils. These catalysts are easily recovered after completion of the reactions, which are carried out either by heating in a sand bath or using microwave irradiation. Comparison of the results obtained with both catalysts indicates that all the reactants examined were oxidized faster on alumina than on silica under these conditions.
Synthesis and Bioactivity of New Phosphorylated R,R’-substituted Sulfoximines
Authors: Reinhard Monica Bellozas , De Licastro Susana  Arnstein
Published: October 2008

R,R’-disubstituted sulfoximines were phosphorylated with O,O–diethylchlorophosphate and phosphorothionate to obtain new organophosphorus compounds. Afterpurification they were characterized by GC-MS and 1H-NMR. The toxicity of thesynthesized O,O-diethyl N-(R,R’-disubstituted sulfoximine) phosphoro-amidothionateswas assayed on Musca domestica. It was found that the methyl phenyl derivative was themost toxic compound, followed by the dipropyl and dibutyl derivatives. The dihexylcompound was the less toxic of all the assayed compounds, being one hundred times lesstoxic than a paraoxon standard The anticholinesterasic activity of the correspondingphosphoramidates was assayed on homogenates of house flies’ heads, giving valuessimilar to paraoxon for the methyl phenyl derivative.
Synthesis and Potent Antimicrobial Activity of Some Novel N-(Alkyl)-2-Phenyl-1H-Benzimidazole-5-Carboxamidines
Authors: Göker Hakan , Alp Mehmet , Yıldız Sulhiye
Published: October 2008

A series of 22 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5- carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activity against S. aureus and methicillin resistant S. aureus (MRSA), E. coli, E. faecalis and for antifungal activity against C. albicans. Compound 59 [1-(2,4-dichlorobenzyl)-N- (2-diethylaminoethyl)-1H-benzimidazole-5-carboxamidine], with a 3,4-dichlorophenyl group at the C-2 position, displayed the greatest activity (MIC = 3.12 μg/mL against both some bacteria and the fungus C. albicans).
N,N’-Substituted 1,2,5 Thiadiazolidine 1,1-Dioxides: Synthesis, Selected Chemical and Spectral Proprieties and Antimicrobial Evaluation †
Authors: Bendjeddou A. , Djeribi R. , Regainia Z. , Aouf N.
Published: October 2008

The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed.
Synthesis, Reactivity and Biological Activity of Novel Bisbenzofuran-2-yl-Methanone Derivatives
Authors: Kirilmis Cumhur , Koca Murat , Cukurovali Alaaddin , Ahmedzade Misir , Kazaz Cavit
Published: October 2008

Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied.
Facile Microwave-assisted Synthesis of 9,10-Dihydro-9,10-ethanoanthracene-11-carboxylic acid Methyl Ester
Authors: Phutdhawong Weerachai , Buddhasukh Duang
Published: October 2008

A facile, high yielding synthesis of 9,10-dihydro-9,10-ethano- anthracene-11- carboxylic acid methyl ester using a modified commercial domestic microwave oven is reported.
Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
Authors: Aragao Valquiria , Constantino Mauricio  Gomes , Beatriz Adilson , José da Silva Gil  Valdo
Published: October 2008

A simple and efficient method for the preparation of 1-methyl-3-oxo-7- oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo- propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl, a simple reagent that was shown to be more efficient, in this case, than commonly used more elaborate methods.
Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation
Authors: Silvia Luiz  F. , Craveiro Marcus V.
Published: October 2008

The oxidation of 2-(3,4-dihydronaphthalen-1-yl)-ethanol (1) with a variety ofthallium(III) salts was investigated. An indan, formed by a ring contraction reaction, wasobtained in good to moderate yields under a variety of reaction conditions: i) thalliumtriacetate (TTA) in aqueous AcOH; ii) thallium tris-trifluoroacetate (TTFA) in aqueousTFA; iii) TTFA in CH2Cl2; iv) thallium tripropionate (TTP) in aqueous propionic acidand v) thallium tris-[(S)-(-)-triacetoxypropionate] in aqueous (S)-(-)-2-acetoxypropionicacid. On the other hand, the reaction of compound 1 with TTA in methanol led to a 2:1mixture of the corresponding cis- and trans-dimethoxylated compounds, respectively.These compounds were formed by a thallium-promoted addition of methanol to thedouble bond.
Synthesis of Novel, Potentially Biologically Active Dibenzosuberone Derivatives
Authors: Merkas Sonja , Litvic Mladen , Cepanec Ivica , Vinkovic Vladimir
Published: October 2008

Novel representatives of the important group of biologically active dibenzosuberone derivatives were prepared: 3,7-dibromo-5-(dimethylaminoethyl- oxyimino)-10,11-dihydro-5H-dibenzo[a,d]cyclohepta-1,4-diene (1), 3,7-dibromo-5-(3- dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (2) and 1,7- dibromo-5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo-[a,d]-cycloheptene (3). These compounds are potential tricyclic antidepressants (TCAs), which are still the most frequently prescribed antidepressants in many countries.
An Efficient Protocol for the Solid-phase Synthesis of Malondiamides
Authors: Vögtle Markus  M. , Marzinzik Andreas L.
Published: October 2008

A novel and straightforward solid-phase synthesis of malondiamides containing a free nitrogen has been developed. These intermediates, which can be directly obtained in good yield and purity, can be further derivatised. This approach can be used for the synthesis of large split-and-mix-libraries.
Cyclization of Free Radicals at the C-7 Position of Ethyl Indole–2-carboxylate Derivatives: an Entry to a New Class of Duocarmycin Analogues
Authors: Al-Said Naim  H. , Shawakfeh Khaled  Q. , Abdullah Wasim N.
Published: October 2008

Aryl free-radicals generated at the C-7 position of ethyl indole-2-carboxylates bearing N-allyl and propargylic groups triggered intramolecular cyclizations to furnish a new class of Duocarmycin analogues, formal ethyl pyrrolo[3,2,1-ij]quinoline-2- carboxylate derivatives, through the less favorable 6-endo-trig cyclization mode.
Chromate Oxidation of α-Nitro Alcohols to α-Nitro Ketones: Significant Improvements to a Classic Method
Authors: Elmaaty Tarek  Abou , Castle Lyle W.
Published: October 2008

A series of eight alkyl and aryl α-nitro ketones were prepared by the potassium dichromate oxidation of the corresponding nitro alcohols. Short reaction times allowed for the easy isolation of pure nitro ketones that are devoid of starting materials and/or other oxidation side products.
Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida
Authors: Sladic Dusan , Gasic Miroslav J.
Published: October 2008

A review of results of bioactivity and reactivity examinations of marine sesquiterpene (hydro)quinones is presented. The article is focused mostly on friedo- rearranged drimane structural types, isolated from sponges of the order Dictyoceratida. Examples of structural correlations are outlined. Available results on the mechanism of redox processes and examinations of chemo- and regioselectivity in addition reactions are presented and, where possible, analyzed in relation to established bioactivities. Most of the bioactivity examinations are concerned with antitumor activities and the mechanism thereof, such as DNA damage, arylation of nucleophiles, tubulin assembly inhibition, protein kinase inhibition, inhibition of the arachidonic cascade, etc. Perspectives on marine drug development are discussed with respect to biotechnological methods and synthesis. Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed.
Criss-cross Cycloadditions on Ketazines Derived from Alicyclic Ketones
Authors: Verner Jiri , Potacek Milan
Published: October 2008

The reactivity of alicyclic ketazines in criss-cross cycloadditions was investigated. They react with potassium cyanate and ammonium thiocyanate in the presence of acetic acid to form spirocyclic perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-diones and perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones, respectively, in relatively high yields.
Synthesis of Some New 2-(3-Aryl-1-phenyl-4-pyrazolyl)-benzoxazoles Using Hypervalent Iodine Mediated Oxidative Cyclization of Schiff’s Bases
Authors: Prakash Om , Pannu Kamaljeet , Kumar Ajay
Published: October 2008

Ten new 2-(3-aryl-1-phenyl-4-pyrazolyl)benzoxazoles have been synthesized by oxidative intramolecular cyclization of the corresponding Schiff’s bases using iodobenzene diacetate in methanol as an oxidant.
Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents
Authors: Jarrahpour Aliasghar , Zarei Maaroof
Published: October 2008

New cis monocyclic β-lactams were synthesized by [2+2] Staudinger cycloaddition reactions of the imine (3,4-dimethoxybenzylidene)-(4-methoxyphenyl)- amine and ketenes derived from different acyl chlorides and Et3N. These monocyclic β-lactams were then cleaved by ceric ammonium nitrate (CAN) to give NH-monocyclic β-lactams, which in turn were converted to N-sulfonyl monocyclic β-lactams by treatment with four different sulfonyl chlorides in the presence of Et3N and 4,4-dimethyl- aminopyridine (DMAP).
Synthesis of Some New bis-Schiff Bases of Isatin and 5-Fluoroisatin in a Water Suspension Medium
Authors: Jarrahpour A. A. , Khalili D.
Published: October 2008

Condensation of aromatic primary bis-amines with isatin (1H-indole-2,3-dione) and 5-flouroisatin occurred cleanly and efficiently in a water suspension mediumwithout using any organic solvent or acid catalyst. The corresponding bis-Schiff baseswere obtained in good yields and were easily isolated by filtration. Their structures wereconfirmed by 1H-NMR, 13C-NMR, IR and mass spectra.
An Efficient Scalable Synthesis of 2,3-Epoxypropyl Phenylhydrazones
Authors: Getautis Vytautas , Daskeviciene Maryte , Malinauskas Tadas , Stanisauskaite Albina , Stumbraite Jolanta
Published: October 2008

A series of mono and di-N-2,3-epoxypropyl N-phenylhydrazones have beenprepared on a large scale by reaction of the corresponding N-phenylhydrazones of9-ethyl-3-carbazolecarbaldehyde, 9-ethyl-3,6-carbazoledicarbaldehyde, 4-dimethyl-amino-, 4-diethylamino-, 4-benzylethylamino-, 4-(diphenylamino)-, 4-(4,4-4'-dimethyl-diphenylamino)-, 4-(4-formyldiphenylamino)- and 4-(4-formyl-4'-methyldiphenyl-amino)benzaldehyde with epichlorohydrin in the presence of KOH and anhydrousNa2SO4.
Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained
Authors: Sapijanskaite Birute , Mickevicius ytautas , Mikulskiene Gema
Published: October 2008

The reactions in benzene of 9-alkyl-3-aminocarbazoles with ethyl-3-oxobutanoateyielded ethyl-3-[(9-alkyl-9H-carbazol-3-yl)amino]but-2-enoate condensation products or N-(9-ethyl-9H-carbazol-3-yl)-3-oxobutanamide acylation products. The condensation productswere cyclized to the corresponding 4,7-dihydro-pyrido[2,3-c]-carbazol-1-ones upon heatingin mineral oil at 240-250 °C. The structures of the synthesized compounds were investigatedby IR, mass spectrometry, 1H- and 13C-NMR spectroscopy and MM2 molecular mechanicsand AM1 semi-empirical quantum mechanical methods.
Synthesis of 2,4,6-Tri-substituted-1,3,5-Triazines
Authors: Afonso Carlos A. M. , Lourenco Nuno M. T. , Rosatella Andreia de A.
Published: October 2008

Several specific synthetic protocols were developed for the preparation from cyanuric chloride of a range of symmetric and non-symmetric di- and tri-substituted 1,3,5-triazines containing alkyl, aromatic, hindered, chiral and achiral hydroxyalkyl, ester and imidazole groups via sequential nucleophilic substitution of the C-Cl bond by C-O, C-N and C-S bonds.