Proceedings
of the 2nd International Conference on the

Chemistry and Biological Activity
of the Synthetic and Natural Compounds

CBC2003

Edited by Prof. V.G. Kartsev Moscow: IBS Press, 2003, vol. 1 - 472 pages, vol. 2 - 352 pages This two-volume publication is a collection of the plenary, oral, and poster presentations at the II International Conference on the Chemistry and Biological Activity of Oxygen- and Sulfur-Containing Heterocycles organized by InterBioScreen Ltd. and Scientific Partnership Foundation, with participation of and support from the Russian Academy of Sciences and the Council on Science and Technology at the Moscow Government. The Conference continues a series of meetings on the Chemistry and Biological Activity of Synthetic and Natural Compounds. The II Conference was greeted by two Nobel Prize winners: Prof. Elias J. Corey (Harvard University, USA) and Prof. Ryoji Noyori (Nagoya

University, Japan). Among the invited lecturers are Prof. A. Katritzki (University of Florida, USA), Prof. R. Hiusgen (University of Munchen, Germany), Prof. van der Plas (University of Wageningen, the Netherlands), and Prof. J. Bergman (Novum Unit of Organic Chemistry, Sweden)-these lecture will appear in the form of separate brochure-as well as other eminent researchers from Great Britain, Belgium, Germany, Greece, India, Italy, the Netherlands, the USA, Sweden, etc. The collection contains the original papers on the chemistry and bioactivity of various O,S-containing heterocycles-from oxiranes and thiiranes to complicate condensed systems-both synthetic and naturally occurring ones. In some papers, much attention is given to the biological activity of
the compounds under consideration and other aspects of practical implementation of O,S-heterocycles, which makes the book interesting not only for synthetic chemists but also for biochemists, pharmacologists, and medicinal chemists.

In parallel, these two volumes will also appear in English, which will enable us to keep the worldwide community well informed about recent advance in the field.

According to our tradition, vol. 2 will be supplemented with some most interesting protocols for synthesis and modification of heterocycles suggested by the researchers from the CIS and Baltic countries of the former Soviet Union in past years.

On behalf of the Organizing Committee, I would like to thank all the participants for their contribution to this book and wish them a success and new achievements.

V.G. Kartsev
Moscow, October 2003

CONTENTS
VOLUME 1

Plenary lectures
Adekenov S.M., Kulyyasov A.T. Synthesis of sesquiterpenoids substituted in the lactone ring	19
Attanasi O.A. Sulphur-containing heterocycles from 1,2-diaza-1,3-butadienes	20
Belen'kii L.I. Preparative chemistry of stable 2H-thiophenium ions	25
Chupakhin O.N., Saloutin V.I, Burgart Ya.V. Synthesis and transformations of fluorine-containing chromones	26
Dearden J.C., Netzeva T.I. QSAR prediction of environmental toxicity of oxygen- and sulphur-containing heterocycles	37
Drach B.S., Brovarets V.S., Smolii O.B., Zyabrev V.S. Recent advance in the chemistry of functionalized oxazoles	52
Florio S., Capriati V., Degennaro L., Luisi R., Perna F. Novel oxazoline-mediated syntheses of heterocycles	66
Granik V.G. O- and S-containing heterocycles as NO donors and NO-synthase inhibitors	72
Kartsev V.G. "Unnatural" naturally occurring heterocycles: The chemistry and bioactivity of O,S-containing secondary metabolites	82
Khilya V.P., Ishchenko V.V. Functionally modified flavonoids, isoflavonoids, coumarins, and related heterocyclic systems	84
Lozinskii M.O., Shelyakin V.V., Demchenko A.M., Shivaniuk A.F. New aspects in the chemistry of O,S,N-containing heterocycles	86
Preobrazhenskaya M.N. Antibacterial glycopeptide antibiotics from N, O-containing macrocycles	88
Saxena A.K. 3D QSAR studies on 5,6-diarylimidazo(2,1-b)thiazole: Selective COX-2 inhibitors	93
Sosnovskikh V.Ya., Usachev B.I. Reaction of 2-trifluoromethylchromones with alkyl mercaptoacetates as a novel redox process with wide synthetic potentialities	104
Tolstikov G.A., Tolstikova T.G., Shults E.E., Sorokina I.V., Chernov S.V., Kharitonov Yu.V. Bioactive higher furanoterpenoids and their derivatives	112
Trofimov B.A. Pyrrolecarbodithioates: Synthesis and application to design of complex heterocyclic systems	127
Voronkov M.G., Shagun L.G., Ermolyuk L.P. 1-Halo-2-organylethane-2-thiones and 1-halo-2-organylethane-2,2-dithiols as precursors of heterocycles	142
Zefirov N.S., Palyulin V.A. Computer-aided drug design	149
Oral presentations
Abashev G.G., Shklyaeva E.V., Lebedev K.Yu. New fluorine-containing and functionalized tetrathiafulvalenes	153
Akhmedzhanova V.I., Ollivier E., Angenot L., Balansard G., Shakhidoyatov Kh.M. Lignans and pyrano(furano)quinolines of Haplophyllum perforatum and their biological activity	157
Akhrem A.A., Gulyakevich O.V., Mikhal'chuk A.L Tautomerism and reactivity of heterocyclic b,b'-tricarbonyls and their anions	161
Basak S.C., Mills D. Modeling of aryl hydrocarbon (Ah) receptor binding affinity for dibenzofurans using the Hierarchical Quantitative Structure-Activity Relationship (HiQSAR) approach	168
Berestovitskaya V.M., Efremova I.E. New polyfunctional systems based on nitrogen-containing thiolene- and thiophene-1,1-dioxides	174
Bozdyreva K.S., Stepanov D.K., Maslivets A.N. 3,2,1-Benzoxathiazine-2,4-diones in synthesis of heterocycles	179
Butin A.V., Dmitriev A.S., Gutnov A.V., Abaev V.T. Furan in synthesis of isochromone derivatives	183
Chernyсh V.P. Derivatives of dicarboxylic acid: Drug design, synthesis, and pharmacological testing	187
Dotsenko V.V., Krivokolysko S.G., Litvinov V.P. Synthesis of condensed sulfur-containing heterocycles from partially hydrogenated pyridines and quinolines	194
Dyachenko V.D., Tkachev R.P. Activated alkoxyethylenes in synthesis of bioactive pyridine and quinoline derivatives	200
Dyatkin A.B., Matthews J.M., Evangelisto M., Gauthier D., Hecker L.R., Hlasta D.J., Hoekstra W.J., Poulter B.L., Maryanoff B.E. Synthesis, resolution, and absolute configuration of novel tricyclic benzodiazepines	201
Erzhanov K.B., Kurmankulov N.B., Batyrbekova A.B. Cyclization of propargyl compounds	205
Fazylov S.D., Gazaliev A.M., Nurkenov O.A. Heterocyclic derivatives of ephedrine alkaloids	206
Firsova O.V., Dolgushina T.S., Polukeev V.A., Ionnisyan E.M., Zavodnik B.E., Stash A.I., Bel'skii V.K., Galishev V.A. Reactions of heterocyclic thione-thiols with 1,3-dipolar reagents	207
Galyautdinov I.V., Ves'kina N.A., Odinokov V.N. Unconventional transformations of 20-hydroxyecdysone and its acetonides leading to formation of oxetane ring	212
Gornostaev L.M., Lavrikova T.I., Arnold E.V., Podvyaznyi O.V. Functionalization of anthraquinone derivatives with aminoalkylamines	214
Grandberg I.I., Nam N.L. Condensed systems based on amino- and oxypyrazoles	217
Hovhannisyan A.Sh., Hovhannisyan Art. Sh., Noravyan A.S. Synthesis of thiothieno[2,3-d]pyrimidines condensed with six-membered heterocycles	219
Ila H. Polarized ketene dithioacetals as versatile building blocks for S-containing heterocycles: A new quinoline synthesis	224
Kaigorodova E.A. 6-Methyl-3,4-dioxo-1H-furo[3,4-c]pyridine-synthetic analog of alkaloid cerpegin: Synthesis, reactions, and biological activity	233
Kamalov G.L., Kotlyar S.A., Grigorash R.Ya., Tkachuk V.V., Chuprin G.N., Shishkin O.V., Konup I.P., Konup L.A. Symmetric and asymmetric dibenzocrown ethers, their derivatives, isomers, and acyclic analogs: Synthesis, structure, and properties	238
Kamat S.P., D'Souza A.M., Paknikar S.K., Dev V., Beauchamp P.S. Biogenetic-type synthesis of (+)-cymbodiacetal, a constituent of Cymbopogon martini	245
Kartsev V.G., Lakeev S.N., Maidanova I.O., Galin F.Z., Tolstikov G.A. Sulfur ylides in synthesis of heterocyclic compounds	251
Khachatryan D.S., Matevosyan K.R., Kazaryan Zh.V., Ugrak B.I. Synthesis and transformations of sulfur-containing five-and six-membered heterocycles	258
Khidyrova N.K., Nishanbaev S.Z., Khodzhaniyazov Kh.U., Kuliev Z.A., Shakhidoyatov Kh.M. Oxygen-containing heterocyclic compounds from Platanus orientalis	261
Kislyi V.V., Demchenko A.M., Kvacheva Z.B., Lozinskii M.O. Derivatives of [1,3,4]thiadiazolo[2,3-c][1,2,4]triazine: A new class of antiviral preparations	264
Kostyanovsky R.G. Saga about Zelinskii dilactones	268
Kovalenko S.N., Chernykh V.P., Zhuravel' I.A., Karasev А.А. Synthesis and reactivity of azacoumarins	279
Kozminykh V.O., Kozminykh E.N. Acylpyruvic acids in synthesis of O- and S-containing heterocycles	286
Krasnov K.A. Barbituric acids in synthesis of new heterocyclic systems. 2. Synthesis of pyrimidine derivatives annelated with O- and S-containing heterocycles	287
Krayushkin M.M. Synthesis of 1,2-dihetarylethenes and their thienyl precursors	289
Kriven'ko A.P., Nikolaeva T.G., Bugaev A.A., Golikov A.G. Furfurylidenearylidenecyclanones: Reactions with N-containing nucleophiles proceeding with preservation or disclosure of furan ring	296
Kur'yanov V.O., Chupakhina T.A., Chirva V.Ya., Grigorash R.Ya., Kotlyar S.A., Kamalov G.L. Crown ethers as catalysts in synthesis of N-acetylglucosamine O- and S-glycosides	300
Lavrenov S.N., Korolev A.M., Turchin K.F., Preobrazhenskaya M.N. Stereo- and regioselective addition of 2- and 3-hydroxymethylindoles to ascorbic and dehydroascorbic acids	305
Lesyk R.B., Zimenkovskii B.S. Biological activity of functionally substituted 4-thiazolidone derivatives	308
Levkovskaya G.G., Bozhenkov G.V., Mirskova A.N. Synthesis of heterocycles from chloro- and bromovinylketones	316
Mamedov V.A., Hamamoto H., Gubaidullin A.T., Komiyama T., Litvinov I.A., Tsuboi S. Reaction of substituted aldehydes with alkyldichloroacetates in conditions of Darzens condensation as effective method for synthesis of O-containing heterocycles	317
Maslivets A.N., Lisovenko N.Yu., Vostrov E.S., Andrakovskii M.V., Novikov A.A. 4,5-Disubstituted 2,3-dihydro-2,3-furandiones: Synthesis and chemical behavior	321
Mironov V.F., Shtyrlina A.A., Varaksina E.N. Reaction of P,P,P-trihalobenzo[d]-1,3,2-dioxaphospholes with substituted acetylenes as a new method for synthesis of benzo[e]-1,2-oxaphosphorines, Р-analogs of natural coumarines	322
Nazrullaev S.S., Khushbaktova Z.A., Syrov V.N., Akhmedkhodzhaeva Kh.S., Saidkhodzhaev A.I. Estrogenic activity of terpenoids from the plants of the Ferula genus	329
Neilands O. 1,3-Dithiolo[4,5-d]pyrimidines: Synthesis and properties	335
Nekrasov D.D. Synthesis and chemical properties of oxazolidine-4,5-diones	343
Nikitchenko V.M., Gorobets N.Yu., Borisov A.V., Kovalenko S.M., Silin O.V., Chuev V.P. Transformation of coumarin derivatives as a synthetic approach to new heterocyclic compounds	344
Paronikyan E.G., Noravyan A.S., Dzhagatspanyan I.A., Arzanunts E.M. Synthesis, transformations, and some neurotropic properties of 2-furylsubstituted condensed thieno[2,3-b]pyridines	348
Pavlov P.T., Shklyaev Yu.V. Synthesis and some transformations of Gewald thiophenes	351
Pivovarenko V.G. 3-Hydroxyflavones as multi-channel fluorescent probes: Design, synthesis, and application	358
Ryndina S.A., Каdushkin А.V., Granik V.G. Pyrimidine cyclization based on 3-amino derivatives of thiophene and pyrrole	364
Salakhutdinov N.F. Synthesis of oxygen-containing heterocycles from terpenoids on the surface of alumosilicate catalysts	365
Shelar A.R., Hilage N.P., Shelar M.A., Rashinkar G.S., Anbhule P.V., Waghmare R.A., Shabadi C.V., Adure A.S. Semisynthetic penicillins	370
Shestopalov A.M. Substituted 2-amino-4H-pyrans: Synthesis, structure, and properties	372
Shikhaliev Kh.S., Medvedeva S.M., Leshcheva E.V., Solov'ev A.S. New sulfur-containing heterocycles based on 2,3-dithiolo[5,4-с]quinoline-2-thiones	373
Shklyaev Yu.V. Synthesis and biological activity of some thiophene derivatives	378
Shults E.E., Vafina G.F., Andreev G.N., Tolstikov G.А. Diels-Alder reaction of 2-isopropenyl-2-thiolene-S,S-dioxide in synthesis of bioactive polycyclanes	384
Shvartsberg M.S., Ivanchikova I.D., Mzhel'skaya M.A. Synthesis of O- and S-containing heterocycles from acetylenic derivatives of quinones	393
Sirakanyan S.N., Paronikyan E.G., Noravyan A.S. New substituted derivates of condensed pyrimidines	398
Suzdalev K.F. Reaction of 4H-pyrans with electrophiles and transformations of reaction products	402
Syrov V.N., Khushbaktova Z.A., Nabiev A.N., Saatov Z. Iridoid glycosides: Structure-activity relationship for toxic injury of liver and perspectives for practical implementation in medicine	411
Tolkunov S.V. Benzothieno[2,3-c]pyridines and benzofuro[2,3-c]pyridines: Synthesis, properties, and biological activity	414
Tolstikova T.G., Sorokina I.V., Shultz E.E., Lazareva D.N. Pharmacological properties of some cyclic sulfones	415
Trishin Yu.G., Konovalova I.V., Burnaeva L.A., Namestnikov V.I., Burangulova R.N., Erofeeva M.R., Mingazovа B.F., Vorob'ev M.V., Dokuchaeva I.S., Litvinov I.A., Bel'skii V.K. Synthesis of novel O,S-containing heterocycles	419
Vasilevsky S.F., Mshvidobadze E.V., Knight D.W Comparative study on heterocyclization of o-acetylenylaryl-, vic-acetylenylpyrazolylcarboxylic, and -hydroxamic acids	426
Veinberg G., Vorona M., Shestakova I., Kanepe I., Lukevics E. Protease-inhibiting ?-lactams: Synthesis and biological activity	433
Velikorodov А.V. Carbamates and their polyfunctional derivatives in synthesis of azaheterocycles	439
Vicini P., Geronikaki A., Incerti M. Aminoderivatives of benzothiazole/benzoisothiazole heterocycles as intermediates in the synthesis of novel therapeutic agents	442
Vizer S.A., Erzhanov K.B. Synthesis of heterocycles upon catalytic intramolecular cyclization and carbonylation of acetylenic compounds	448
Volovenko Yu.M., Khilya О.V., Volovnenko Т.А. 2-Hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles as new polyfunctional reagents	449
Yanchenko V.A., Demchenko A. M., Gur'eva A.N., Bukhtiarova T.A., Lozinskii M.O. Derivatives of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine: Synthesis and properties	453
Yu V.K., Fomicheva Y.Y., Mukhasheva R.D., Klepikova S.G., Praliev K.D., Berlin K.D. Hetero(thia, oxa)cycles containing an N-alkoxyalkylpiperidine moiety	457
Zhuravel' I.A., Karasev А.А., Kovalenko S.N., Chernykh V.P. Chemistry of azacoumarins	460
Post presentations
El-Kashef H.S. Polyfused heterocycles via the Clauson-Kaas reaction	463
Goksel F.S., Ibis C., Akgun N. Novel cyclic and acyclic sulfur compounds from p-chloranil	464
Vicini P., Incerti M., Maggiali C.A., Ricci, A., Rolli E. Convenient synthetic approach to N,O-containing heteroarylureas, potential plant-growth regulators	465
Yavari I., Jabbari A., Moradi Sh. An ab initio study on conformational properties of lenthionine	466
Author index	467-470

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