Proceedings
of the III International Conference on the


Chemistry and Biological Activity
of Synthetic and Natural Compounds

CBC2006

 

Edited by Prof. V.G. Kartsev

Moscow: Published by the International Charitable Scientific Partnership Foundation (ICSPF), 2006, vol. 1 - 504 pages, vol. 2 - 424 pages

In the opinion of the leading experts both at home and abroad, the series of international conferences on The Chemistry and Biological Activity of Synthetic and Natural Compounds (CBC) has become one of the most important and representative forums on the chemistry and bioactivity of heterocycles held in Russia. The first one, -2001, Moscow, was devoted to the chemistry of nitrogen-containing heterocycles and alkaloids; the second conference -2003, Moscow, dealt with the chemistry and bioactivity of O,S-containing heterocycles. The major organizers and sponsors of these conferences were InterBioScreen Ltd. and the International Charitable Foundation Scientific Partnership (ICSPF).

The tradition of these scientific forums was carried on by organizing the III International Conference on The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles (CBC-2006) at the Russian Academy of Sciences' Research Center at Chernogolovka. The conference was dedicated to the 90th anniversary of Professor. Alexey Kost's birthday, an outstanding scientist and remarkable educator, Honored Scientist of the Russian Federation. This conference was organized with the participation and support from the Russian Academy of Sciences, Russian Mendeleev Chemical Society, Moscow State University, and Council on Science and Technology under the Moscow Government.

Among invited plenary lecturers are Prof. H.C. van der Plas (University of Wageningen, the Netherlands), Prof. J. Bergman (Novum Unit of Organic Chemistry, Sweden), Prof. M. Mąkosza (Institute of Organic Chemistry, Warsaw, Poland), Prof. L. Fišera (Slovak University of Technology, Bratislava, Slovak Republic), Prof. Atta-ur-Rahman (International Center for Chemical Sciences, University of Karachi, Pakistan), and other noted scientists from Austria, Belgium, France, Germany, Great Britain, Greece, India, Italy, Jordan, the Netherlands, Russia, Sweden, the USA, and the CIS countries (republics of the former Soviet Union).

The words of greetings were received from the Noble Prize laureates Prof. Elias J. Corey (Harvard University, USA) andProf. Jean-Marie Lehn (Institut de Science et d'Ingénierie Supramoléculaires, France).

This two-volume collection presents the full Proceedings of the III International Conference on The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and containsplenary lectures, oral and poster presentations. These are the original papers submitted by scientists, from both this country and abroad, on the synthesis, chemical transformation, and biological activity of nitrogeneous heterocycles, from simple to complicated condensed systems.

These two volumes are published in Russian and English. To keep with our tradition, vol. 2. is supplemented with the most interesting selected synthetic protocols for the preparation and modification of heterocycles developed in the last few years by chemists in Russia, Ukraine, Belarus, etc. Most of these works were inspired and supported by InterBioScreen.

On behalf of the organizers, I would like to thank all the participants for their contribution to this collection.

Alexey Nikolaevich Kost was my esteemed Teacher. For me, it is of special value that the International Conference -2006 has made it possible for scientists from more than 30 countries across the world to get together and pay tribute to this outstanding person, scientist, and edicationalist.

Victor Kartsev,Dr. Sc., Prof.
Chairman, CBC-2006 Organizing Committee
President, Scientific Partnership Foundation
Chairman, Board of directors of InterBioScreen

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The Chemistry and Biological Activity
of Synthetic and Natural Compounds




NITROGEN-CONTAINING HETEROCYCLES

Edited by Prof. V.G. Kartsev

Volume 1




ICSPF
Moscow-2006

The Chemistry and Biological Activity
of Synthetic and Natural Compounds




NITROGEN-CONTAINING HETEROCYCLES

Edited by Prof. V.G. Kartsev

Volume 2




ICSPF
Moscow-2006

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CONTENTS
VOLUME 1

 
Plenary lectures

Akhrem A.A., Gulyakevich O.V., Mikhal'chuk A.L.
[2+4]-Cyclocondensation of monocyclic azomethines with β-di-
and β,β'-tricarbonyl compounds in synthesis of azangular heterocycles
15
Atta-ur-Rahman, Choudhary M.I.
Nitrogen-containing heterocycles from natural sources:
Isolation, biological studies, and synthesis
20
Bergman J., Stensland B.
Cyclization of cyanoethylated ketones as a route to 6-hydroxylated
indole derivatives
28
Chupakhin O.N., Rusinov V.L., Charushin V.N.
Abnormal nucleosides from isosteres of purine
33
Elguero J.
The structure of pyrazoles in the solid state: Static and dynamic aspects
41
Fišera L.
Control of regio- and stereoselectivity in nitrone cycloadditions
and their utilization in synthesis
46
Florio S.
o
-Lithiation of aziridines and oxiranes as a useful synthetic methodology
51
Granik V.G.
Biotransformations of heterocyclic nitrogen-containing drugs
53
Hajós Gy.
Zwitter-ionic heterocycles: A pool of novel polyfused ring systems
63
Jordis U.
How to use software and integrate databases in the daily practice
of heterocyclic chemist
67
Kostyanovsky R.G.
Nitrogen chirality in heterocyclic chemistry
72
Krasnov K.A., Kartsev V.G.
-reactions of cyclic b-dicarbonyls in the chemistry of quinoline
and isoquinoline systems
76
Mąkosza M.
Synthesis of indoles via nucleophilic substitution of hydrogen in nitroarenes
104
Poroikov V.V., Filimonov D.A., Gloriozova T.A., Lagunin A.A.
Computer-aided prediction of biological activity for nitrogen-containing
organic compounds
109
Preobrazhenskaya M.N.
Chemistry and biology of ascorbigen
115
Sagitullina G.P., Sagitullin R.S.
Recyclization of pyridinium salts: New horizons
121
Saloutin V.I., Burgart Ya.V., Chupakhin O.N.
Design of azaheterocycles based on fluorine-containing
2,4-dioxobutanoates and their derivatives
129
Saxena A.K.
Substituted arylpiperazines in rational drug design
135
Shestopalov A.M., Rodinovskaya L.A., Shestopalov A.A.
Recyclization reactions of degenerate carbo- and heterocycles:
Practical retrosynthetic approach to new multicomponent methods
for synthesis of N-containing five- and six-membered heterocycles
146
Vasilevsky S.F., Balova I.A.
New one-pot synthesis and heterocyclization of vic-functionalized aryl(hetaryl)alkadiynes-1,3
156
 

Oral presentations

Abdou W.M., Sediek A.A.
Biologically important N-heterocycles and their phosphono derivatives
163
Abu-Orabi S.T.
1,3-Dipolar cycloaddition reactions in synthesis of heterocycles
164
Adekenov S..
Nitrogen-containing derivatives of natural sesquiterpene lactones
167
Agarwal S., Filali S., Fröhner W., Knöll J., Krahl M.P.,
Reddy K.R., Knölker H.-J.

Application of oxidative cyclizations to the synthesis
of bioactive nitrogen-containing heterocycles

176

Akhmetova V.R., Nadyrgulova G.R., Khairullina R.R., Khafizova S.R., Kunakova R.V., Dzhemilev U.M.
One-pot synthesis of novel N,S-containing heterocycles

187

Aripova S.F., Zhalolov I.Zh., Levkovich M.G., Tashkhodzhaev B.,
Khuzhaev V.U., Mirzaev Yu.R.

New alkaloids from Arundo donax L. for medicinal applications

190

Atazhanova G.A.
N,S-containing terpenoid heterocycles from essential oil of plants
195
Bazureau J.P., Legeay J.C., Fraga-Dubreuil J., Hakkou H.
Ionic liquid-phase technology: A new tool for combinatorial chemistry. Applications in heterocyclic chemistry mediated by microwave
dielectric heating
203
Beccalli E.M., Broggini G.
Pd-Promoted intramolecular formation of CN bonds
in synthesis of heterocyclic systems
206
Belous A.R.
Endogenous indole compounds: Biological significance
of 5-hydroxytryptamine in health and diseasefuture of drug discovery
209
Berestovitskaya V.M., Anisimova N.A., Makarova N.G.
Synthesis of nitrogen-containing heterocycles
from b-nitroethenylphosphonates and -carboxylates
213
Bölcskei H., Gács-Baitz E., Szántay Cs. Jr., Kalaus Gy., Szántay Cs.
Synthesis of indoloazepines and indoloazocines
215
Burgart Ya.V., Pryadeina M.V., Khudina O.G., Saloutin V.I., Chupakhin O.N.
Synthesis of fluoroalkyl-containing pyrimidines
219
Chung M.C.
Prodrug design: Improving drug activity
223
Danagulyan G.G.
KostSagitullin rearrangement with amine exchange
and concurrent recyclization of pyrimidinium salts
228
Dondoni A., Massi A.
Multicomponent syntheses of glycoside-decorated N-heterocyclic pharmacophores
231
Drach B.S., Sviripa V.N., Pil'o S.G., Popil'nichenko S.V.,
Golovchenko A.V., Brovarets V.S.

Functionalized condensed heterocycles from 2-acylamino-
3,3-dichloroacrylonitriles

236

Duburs G., Bisenieks E., Krauze A., Plotniece A., Sobolevs A.,
Tirzitis G., Vigante B.

Dihydropyridines as biomimetics and bioprotectors

239

Dzvinchuk I.B., Lozinskii M.O.
2-Acylmethyl-1H-benzimidazoles and 2-phenacylbenzothiazole
in synthesis of heterocyclic compounds
243
Dzvinchuk I.B., Lozinskii M.O.
2-Phenacylbenzothiazole and 2-acylmethyl-1H-benzimidazole hydrazones: Synthesis, structure, cyclization, and recyclization
249
Eremkin A.V., Mol'kov S.N., Ershov O.V.
Hydrolysis of cyano groups in 2-halo-6-hydroxy-5,5-dialkyl-
5,6-dihydropyridine-3,4,4(1H)-tricarbonitriles
256
Ershov A.Yu., Lagoda I.V., Koshmina N.V., Dobrodumov A.V.
Recyclization of isoxazole derivatives
259
Fisyuk A.S., Mukanov A.Yu.
Domino reactions in synthesis of pyrimido[6,1-a]isoquinolines
and pyrimido[6,1-a]-b-carbolines
262
Geronikaki A., Incerti M., Zani F., Vicini P.
2-Benzo[d]isothiazolylimino-5-arylidene-4-thiazolidinones:
Synthesis and antimicrobial activity
268
Gidaspov A.A.
bis
-Trinitromethylation of 2,4,6-trichloro-1,3,5-triazine
272
Gornostaev L.M., Arnold E.V., Beresnev V.A., Dolgushina L.V.,
Lavrikova T.I., Sokolova M.S.

Anthraquinone derivatives condensed with pyrrole and triazole rings:
Synthesis and properties

275

Gorobets N.Yu., Ermolaev C.A., Dzhavakhishvili S.G.,
Sirko S.N., Chernenko V.N., Desenko S.M.

2-Dimethylaminomethylene-1,3-cyclohexanedione derivatives
in reaction with methylene-active nitriles

278

Granzhan A., Ihmels H., Viola G.
Rearrangements in diazoniapentaphenes and
DNA-binding properties of diazoniapolycycles
282
Gulyakevich O.V., Mikhal'chuk A.L.
Construction of azinone framework by [3+3]-cyclocondensation
of b-enaminones with β-ketoesters
286
Isak A.D., Pogorelova I.P., Tyupalo N.F., Isak V.A.
Pyrimidine sulfone amides and their derivatives:
Synthesis and biological activity
290
Kalinin V.N., Shishkov I.V., Moiseev S.K., Shults E.E., Tolstikov G.A.
Synthesis of new dienes and trienes of the morphinan series
293
Klochkova I.N., Sazonov A.A.
Functionally substituted hydrogenated azines and thiazines:
Synthesis and characterization
296
Kofanov E.R., Sosnina V.V.
Multifunctional heterocyclic compounds from nitriles
of aromatic carboxylic acids
299
Korotkikh N.I., Raenko G.F., Kiselev .V., Knishevitsky .V., Shvaika .P., Glinyanaya N.V., Panov I.S., Cowley .H., Jones J.N., Moore J.A.
Stable carbenes. Insertion into і bonds and reaction with ester function.
New cleavage and thermal transformation of 1,2,4-triazol-5-ylidenes

301

Kovalenko S.N., Silin .V., Savchenko .I.
Synthesis and reactivity of pyrazolo[4,3-c]quinolines
305
Kravchenko A.N., Sigachev A.S., Chikunov I.E., Lozhkin B.V., Baranov V.V., Gazieva G.A., Trunova N.S., Lysenko K.A., Belyakov P.A., Makhova N.N.
New horizons in α-ureidoalkylation

309

Kur'yanov V.O., Priskoka U.S., Chupakhina T.A., Chirva V.Ya.,
Katsev A.M., Shishkin O.V., Shishkina S.V., Kotlyar S.A., Kamalov G.L.

Heteroaromatic glycosides of neutral and amino saccharides:
Synthesis, structure, and biological activity

312

Lesyk R.B., Zimenkovsky B.S., Atamanyuk D.V.
Thiopyrano[2,3-d]thiazoles and their derivatives:
Synthesis and biological activity
317
Levinson F.S., Ermolaeva E.A., Efimov S.I., Evgen'ev M.I.,
Varganov R.V., Vasyutina E.A., Shakirova I.M.

4,6-Dichloro-5,7-dinitro- and 4-methoxy-6-chloro-5,7-dinitrobenzo-
furazans as new two-position electrophiles

321

Levkovich M.G.
Electric charge on atoms and physicochemical properties of alkaloids
324
Levkovskaya G.G., Bozhenkov G.V., Savosik V.A., Mirskova A.N.
Derivatives of 4- and 5-halopyrazoles:
Targeted synthesis, structure, and properties
327
Likhacheva N.A., Gataullin R.R., Khusnutdinov R.N.,
Abdrakhmanov I.B., Tolstikov G.A.
Synthesis of 3-methyleneindoles and their analogs from alkenylanilines

330

Makarenko S.V., Berestovitskaya V.M., Sadikov K.D.,
Tafeenko V.A., Chernyshev I.V.

Potentially bioactive 1,4-benzodiazinones and their heteroanalogs:
Synthesis and structure

335

Makhova N.N., Shevtsov A.V., Petukhova V.Yu.,
Kuznetsov V.V., Kislukhin A.A.

Transformation of diaziridine ring under the action of ketenes
as a new synthetic approach to nitrogen-containing heterocyclic systems

337

Mali A., Shelar M., Shelar A.
Antibiotic resistance: A search for new b-lactam antibiotics
339
Mamedov V.A., Khafizova E.A.
Chelate azolo[a]annelated qunoxalines from phenylhalopyruvates
and their structural analogs
342
Mareev A.V., Pavlov D.V., Khatashkeev A.V., Medvedeva A.S.,
Afonin A.V., Ushakov I.A.

Cascade assembling of polyfunctional 1,2-dihydropyridine and related compounds from 3-trimethylsilyl-2-propynal and 2-aminopyridine
under microwave activation

345

Medvedeva A.S., Demina M.M., Novokshonov V.V.,
Safronova L.P., Rulev A.Yu., Pavlov D.V., Mareev A.V., Afonin A.V.
Synthesis of azidomethyl-1-1,2,3-triazoles

350

Mikhalev O.V., Tarasevich B.N., Fedyanin I.V., Il'ina I.G.
Autocomplexes of nitroaryls with heterocycles:
Synthesis and characterization
355
Mirzaev Yu.R.
Imperialine derivatives: M2-Cholinoblocking activity and perspectives
357
Mirzaev Yu.R.
Hypotensive ester alkaloids of Veratrum: Problems of clinical implementation
359
Mirzaev Yu.R., Kazantseva D.S., Rakhimov Sh.B., Vinogradova V.I.
New N-benzyl-cytisines: Preliminary pharmacological testing
364
Musienko .., Dybenko .G., Kartsev V.G.
Benzo analogs of cuscutamine and canthine
367
Nekrasov D.D.
N-Cyanation of azaheterocycles and their use as syntonization agents
371
Nekrasov D.D., Obukhova A.S.
2-Amino-substituted 6-aryl-1,3-oxazin-4-ones:
Synthesis and biological activity
380
Nemes A.
Synthetic studies on derivatives and metabolites of cis/trans-apovincamine
383
Nosova E.V., Lipunova G.N., Laeva A.A., Charushin V.N.
Fluorinated 2-substituted [1,3]benzothiazinones: Synthesis and properties
389
Ol'shevskaya V.A., Zaitsev A.V., Savchenko A.N.,
Luzgina V.N., Shtil' A.A., Kalinin V.N.

Carboranylporphyrins: Synthesis and bioactivity

392

Paronikyan E.G., Noravyan A.S., Hakobyan Sh.F.
New condensed thieno[3,2-d]pyrimidines and thieno[3,2-d]-1,2,3-triazines: Synthesis and bioactivity
396
Plaskon' A.S., Ryabukhin S.V., Volochnyuk D.M., Tolmachev A.A.
3-Formylchromones in recyclization with 1,3-CCN-
and 1,3--binucleophiles
398
Polygalova N.N., Mikhailovskii A.G., Vakhrin M.I.
Carbonyl derivatives of condensed isoquinolines: Synthesis and reactivity
402
Popkov S.V., Kovalenko L.V.
1-Azolylmethyl-6-benzylidene-2-alkoxy-2-methyl-
and 2,2-dimethylcyclohexanols: Synthesis and bioactivity
406
Przheval'skii N.M.
Heterohexadiens in synthesis of heterocycles
410
Rádl S., Klecán O.
New synthetic routes to triptanes
412
Samsoniya Sh.A., Trapaidze M.V., Gogrichiani E.O.,
Katsadze E.A., Maisuradze J.P., Dzhaparidze K.G.

Some spiro derivatives of indole and condensed bis-indoles

417

Semenov V.E., Nikolaev A.E., Giniyatullin R.Kh., Lodochnikova O.A., Voloshina A.D., Galiullina L.F., Latypov Sh.K., Reznik V.S.
Pyrimidinophanes with nitrogen atoms in bridging groups:
Synthesis and properties

422

Shelyakin V.V., Kartsev V.G., Vorob'ev D.V., Lozinskii M.O.
Tandem reactions of some metabolites of natural compounds
425
Shestakov A.S., Gusakova N.V., Shikhaliev Kh.S.
Cyanamides and their derivatives in reactions of heterocyclyzation
431
Shikhaliev Kh.S., Kryl'skii D.V., Falaleev A.V.,
Kovygin Yu.A., Potapov A.Yu.

Construction of heterocyclic systems from guanidines and carbonyls

434

Shklyaev Yu.V., Glushkov V.A., Stryapunina O.G.,
Rozhkova Yu.S., El'tsov M.A.

Dearomatization of methoxy- and methylarenes
as a novel synthetic route to spiro-heterocycles

436

Sirakanyan S.N., Kartsev V.G., Paronikyan E.G., Noravyan A.S.
Derivatives of 2,7-naphthyridine: Synthesis, transformations, and bioactivity
446
Stroganova T.A., Vasilin V.K., Krapivin G.D.
Amino acids of the thieno[2,3-b]pyridine series in reactions
of intramolecular cyclization
449
Suzdalev K.F., Babakova M.N., Den'kina S.V, Kartsev V.G.
Indoles bearing reactive groups for synthesis of combinatorial libraries
452
Usova .B., Lysenko L.I., Krapivin G.D.
2-Hydroxy-4- and -6-furylacetophenones, furylbenzazines, and azoles:
Synthesis and properties
457
Van der Eycken E.
Microwave irradiation: A 'green tool' in 2(1H)-pyrazinone chemistry
460
Veinberg G., Vorona M., Shestakova I., Kanepe I., Lukevics E.
Antitumor compounds from 3-alkylidene-2-azetidinone as a template
464
Velikorodov .V.
Quinones and quinoids in synthesis and modification of indoles
466
Vizer S.A., Dedeshko E.H., Erzhanov K.B., Dembitskii V.M.
Synthesis of N-containing heterocycles from a-propargyl-
b-dicarbonyls and their O-phosphoryl derivatives
469
Volochnyuk D.M., Pushechnikov A.O., Pinchuk A.M., Tolmachev A.A.
Fused 1,5,2-diaza- and 1,5,2-oxazaphosphinines: Synthesis and properties
474
Voskressensky L.G., Vorob'ev I.V., Varlamov A.V.
Unusual reactions of tetrahydrobenzo[b][1,6]naphthyridines
with activated alkynes
480
Zobov V.V., Semenov V.E., Kataev V.E., Akamsin V.D., Reznik V.S.
Tetraalkylammonium derivatives of uracil and their macrocyclic analogs
as potential neuromuscular transmission modulators
482
 
Author index
485488

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CONTENTS
VOLUME 2

Poster presentations
5-288
Selected synthetic protocols
289-412
Author index
413-420

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