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



ATTENTION !

This CD edition for the FIRST TIME makes it possible to work in ISIS.2 - search format by both textual (author/s, paper title) and structural fragments. Included DB contains 603 information units describing over 2,800 chemical formulae and over 1500 reactions.
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The Chemistry and Biological Activity
of Synthetic and Natural Compounds




OXYGEN- AND
SULFUR-CONTAINING HETEROCYCLES


Edited by Prof. V.G. Kartsev

Volume 1


         

Moscow 2003
IBS PRESS

The Chemistry and Biological Activity
of Synthetic and Natural Compounds




OXYGEN- AND
SULFUR-CONTAINING HETEROCYCLES


Edited by Prof. V.G. Kartsev

Volume 2


         

Moscow 2003
IBS PRESS

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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
Cherny˝h 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 └.└.
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, đ-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., ╩Ódushkin └.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-˝]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.└.
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., MingazovÓ 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 └.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 ╬.V., Volovnenko Ď.└.
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 └.└., 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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CONTENTS
VOLUME 2

Post presentations
5-228
Selected synthetic procedures
229-338
Author index
339-345

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