Proceedings
of the I International Conference on


"The Chemistry and Biological Activity
of Nitrogen-Containing Heterocycles and Alkaloids"
CBC2001



V.G. Kartsev, G.A. Tolstikov (Editors)

Moscow: Iridium Press, 2001, vol. 1 - 568 pages, vol. 2 - 472 pages

This two-volume publication is a collection of plenary lectures, oral presentations, and posters presented at the I International Conference on the Chemistry and Biological Activity of Nitrogeneous Heterocycles organized and sponsored by InterBioScreen Ltd. and Foundation Scientific Partnership with participation and support of the Russian Academy of Sciences, Moscow State University, and the Council on Science and Technology at Moscow Government.

This conference opens a series of annual meetings on the Chemistry and Biological

Activity of Synthetic and Natural Compounds and is devoted to the most capacious and interesting branch of chemistry-synthetic nitrogeneous heterocycles and their natural counterparts, alkaloids.

The organizers aimed at gathering together synthetic chemists, experts in the chemistry of natural compounds, medicinal chemists and pharmacologists, and thus to eliminate the barriers of disciplinary specialization and provide the opportunity for participants working in different areas of the chemistry of biologically active compounds to discuss current trends in this many-sided branch of science.

In view of the scientific importance of presented materials and their interdisciplinary character, the Organizing Committee found it reasonable to publish them in the form of full-format reviews (plenary lectures), papers (oral presentations), and brief communications (poster presentations). This has led to this two-volume publication which we hope will give a start to periodic edition of the proceedings of forthcoming conferences.

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

The book also contains a section containing 100 most interesting methods for synthesis and modification of heterocycles developed by the workers from CIS and Baltic countries of the former Soviet Union in several past years. The number of papers submitted to this section was so large that Scientific Partnership has decided to publish a periodic collection of such materials in between the conferences.

The next meeting of the series will be devoted to oxygen-containing heterocycles, natural flavonoids, iridoids, and coumarins.

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


V.G. Kartsev
Moscow, August 2001


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The Chemistry and Biological Activity
of Nitrogen Containing Heterocycles and Alkaloids




NITROGEN-CONTAINING HETEROCYCLES
AND ALKALOIDS

V.G. Kartsev, G.A. Tolstikov
(Editors)

Volume 1



Iridium Press
Moscow
2001

The Chemistry and Biological Activity
of Nitrogen Containing Heterocycles and Alkaloids




NITROGEN-CONTAINING HETEROCYCLES
AND ALKALOIDS

V.G. Kartsev, G.A. Tolstikov
(Editors)

Volume 2



Iridium Press
Moscow
2001

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CONTENTS
VOLUME 1


Plenary lectures

11-198

Adekenov S.M.
Perspectives for development of new drugs based on alkaloids and nitrogen-containing terpenoids

13
Akhrem A.A., Gulyakevich O.V., Mikhal'chuk A.L.
Synthesis of condensed quinolizine derivatives through annelation of cyclic Schiff bases: [2+4]-cyclocondensation

19

Andronati S.A., Makan S.Yu.
Nitrogen-containing heterocyclic compounds as ligands for serotonin receptors

33

Belen'kii L.I., Poddubnyi I.S., Luiksaar S.I., Krayushkin M.M.
Trichloromethylarenes in synthesis of 1,3,4-oxadiazoles

44

Charushin V.N., Chupakhin O.N.
Ortho, meta- and para-cyclization in structural modification of p -deficient azaaromatics

51

Chupakhin O.N., Fedorova O.V., Rusinov G.L.
Lipophilic nitrogenous heterocycles as a promising class of antituberculosis agents

65

Dovlatyan V.V.
Reactions of functionally substituted azines

75

Drach B.S., Brovarets V.S., Smolii O.B.
Phosphonium reagents for synthesis of nitrogen-containing heterocycles

83

Elyakov G.B., Radchenko O.S., Balaneva N.N., Novikov V.L.
Marine alkaloids: Chemistry and pharmacology

93

Granik V.G.
Nenitzescu reaction: A new approach to synthesis of annelated 5-hydroxy-indoles and -benzofurans

94

Ivin B.A.
New reactions of heteroazines as a route to bioactive azoles and azines

101

Kartsev V.G.
Biological activity and new trends in the chemistry of isoquinoline alkaloids

110

Khilya V.P., Kupchevskay I.P., Grishko L.G.
Reactions of modified isoflavones with hydrazine and its derivatives

118

Khoshtariya T.E.
Synthesis, properties, and biological activity of benzo[b]furo-, benzo[b]-thiophene-, dioxodihydro-1H-benzo[b]furo-, dioxohydro-1H-benzo[b]-thiopheneindoles and their derivatives

125

Kostyanovsky R.G., Kostyanovsky V.R., Kadorkina G.K., Torbeev V.Yu.
New routes to chiral drugs

132

Makriyannis A.
Heterocyclic probes for studying the endocannabinoid biochemical system

137

Mezheritskii V.V.
Chemistry of 1H-1,2-diazaphenalene

139

Poroikov V.V., Filimonov D.A.
Computer-assisted prediction of biological activity in a search for and optimization of new drugs

149

Praliev K.D.
T- and N-substituted mono- and bicyclic pyperidines: Synthesis, stereochemistry, transformations, and properties. New synthetic analgetics and anesthetics

155

Shults E.E., Tolstikov G.A., Shakirov M.M., Tolstikova T.G.
Synthesis of thebaine-derived m -opioid receptor agonists

161

Shakhidoyatov Kh.M.
Chemical transformations of tricyclic quinazoline alkaloids

167

Tolstikov G.A., Shults E.E., Chernov S.V., Tolstikova T.G., Sorokina I.V., Shakirov M.M., Mamatyuk V.I.
Synthesis of alkaloid-like compounds from diterpenic acids: A new group of nootropic agents

179

Yunusov M.S.
Alkaloids as biologically active compounds

186

Zefirov N.S., Palyulin V.A.
Quantitative structureÍactivity relationship studies on nitrogen-containing heterocyclic compounds

194

Oral presentations

199-560

Abdrakhmanov I.B., Gataullin R.R., Afon'kin I.S., Minnigulov F.F.
Heterocyclization of alkenyl anilines: New methods

201

Akhmedzhanova V.I., Shakirov R.Sh., Rezhepov Zh.
Oxytropis alkaloids

206

Aliev N.A.
Autocondensation of chloroacetanilides into 1,4-bis(aryl)-2,5-diketopiperzines

210

Atroshchenko Yu.M., Shakhkel'dyan I.V.
Synthesis of 3-azabicyclo[3,3,1]nonane derivatives from aromatic nitro compounds

212

Berestovitskaya V.M., Zobacheva M.M., Novikov B.M., Vasil'eva O.S., Usik N.V., Aleksandrova S.M., Tyurenkov I.N.
Synthesis and structure of 2-oxo-1-pyrrolidinylacetamides

216

Borodulin V.B.
Interaction of transition metal complexes containing nitrogeneous heterocycles with nucleic acids: Biochemical aspects

221

Butin A.V., Stroganova T.A., Smirnov S.K.
New opportunities for synthesis of mitosenes, mitomycins, and antitumor drug EO-9

223

Buzykin B.I., Eliseenkova R.M., Badrtdinova O.I., Avvakumova L.V., Zyablikova T.L., Gubaidullin L.T., Litvinov I.A.
Tautomerism of hydrazinoazine derivatives

226

Chashchikhina S.Z., Potapov G.P.
Synthesis and characterization of water-soluble low- and high-molecular hemin compounds

231

Chupakhin O.N., Kozhevnikov D.N., Kozhevnikov V.N., Rusinov V.L., Raevskii K.S., Narkevich V.B.
Synthesis of amino-1,2,4-triazines as potential anticonvulsive agents

234

Danagulyan G.G.
An unconventionalnal synthetic route to polysubstituted 2-alkylaminonicotinamides

236

Demchenko A.M., Bukhtiarova T.A., Nazarenko K.G., Lozinskii M.O.
Analgesics of new generation on the basis of condensed quaternary imidazolium salts

242

Dzhakhangirov F.N.
Diterpenoid alkaloids: A new class of natural compounds with anti-arrhythmic activity

247

Dzhakhangirov F.N., Salimov B.T., Yunusov M.S.
StructureÍactivity relation for lycoctonine alkaloids and their analogs

250

Erzhanov K.B., Vizer S.A., Kurmankulov N.B., Dedeshko E.Kh.
N-Acetylene derivatives of aromatic amines in synthesis of nitrogeneous heterocycles

252

Fisyuk A.S., Ryzhova E.A.
New reactions of cotarnine with CH and NH acids

254

Galin F.Z., Lakeev S.N., Mullagalin I.Z., Maidanova I.O., Tolstikov G.A.
New synthesis of indolizidindione and pyrrolizidindione derivatives from amino acids

256

Galishev V.A., Dolgushina T.S., Shubnikov A.M., Labeish N.N., Bel'skii V.K.
Triaza-l 5-phosphorines: Novel phosphorus- and nitrogen-containing heterocycles

263

Gazaliev A.M., Fazylov S.D., Nurkenov O.A., Kasenov R.Z., Zhurinov M.Zh.
Search for and screening of new bioactive compounds among commercially available alkaloids

268

Golod E.L., Saraev V.V., Gavrilov A.S., Tsypin V.G., Amandurdyeva A.D.
Synthesis and reactions of N-adamantylazoles

271

Gornostaev L.M., Arnold E.V., Bulgakova N.A., Lavrikova T.I., Mitrokhin R.V., Podvyaznyi O.V., Sakilidi V.T.
Novel nitrogen-containing quinoid heterocycles: Synthesis and application

277

Isak A.D., Pogorelova I.P.
Transformation of naphthalic anhydride into derivatives of benz[c,d]indolin-2-one

282

Kagarlitskii A.D., Iskakova M.K., Turmukhambetov A.Zh.
Catalytic synthesis of nicotinonitrile from pyridine alkaloids

286

Kagarlitskii A.D., Krichevskii L.A., Balpanov D.S.
Synthesis of 2-methylpyrazine

288

Kalinichenko E.N., Podkopaeva T.L., Mikhailopulo I.A., Player M.R., Torrence P.F.
Influence of heterocyclic nitrogen atom (N1) and exocyclic amino moieties (NH2C6) in deazaadenosine analogs 2-5A on the activation of RNase L

291

Kalinin V.N.
New trends in the chemistry of sydnones

295

Kaminskii V.A., Slabko O.Yu., Verbitskii G.A., Ageenko N.V.
Synthesis and properties of quinonoid derivatives of pyrido[1,2-a]benzimidazole and related compounds

301

Khachatryan D.S., Matevosyan K.R.
1,2-Dihydro-4-quinazolinones: Synthesis and properties

306

Khuzhaev V.U., Zhalolov I., Aripova S.F., Mirzaev Yu.R., Kurmukov A.G.
Chemistry, transformations, and pharmacological activity of Arundo donax L. alkaloids

311

Klochkova I.N., Semenova N.N., Sazonov A.A.
Synthesis and biological activity of functionally substituted heterocyclic perhydroazines and perhydroazoles

314

Kobrakov K.I., Dmitrieva M.B., Kondratkov V.T., Bocharnikova V.A., Stankevich G.S., Rybina I.I., Kobrakov I.K.
Target synthesis of biocide compounds containing five- and six-membered nitrogeneous heterocyclesÎpromising bioprotectors for textile stuffs

319

Korotkikh N.I., Losev G.A., Shvaika O.P.
Synthesis and biological activity of heterocyclic compounds with chalcogen-containing small rings

323

Koz'minykh V.O., Igidov N.M., Koz'minykh E.N., Berezina E.S.
1,3,4,6-Tetracarbonyls and related compounds containing overcrowded a - and b -dioxo fragments: Synthesis, structure, nucleophilic reactions, and biological effects

328

Krasnikov V.V., Mil'gizina G.R., Tyurin R.V., Minyaeva L.G., Mezheritskii V.V.
Bis-heterocyclization of acid hydrazides with ethoxymethylene derivatives of heterocyclic -aminonitriles and related reactions

333

Krasnov K.L., Gorovoi A.S., Kartsev V.G.
Aminomethylation of 5-substituted barbituric acids. Mannich bases containing the fragments of cytisine and salsolidine alkaloids: Synthesis and structure

338

Kriven'ko A.P., Reshetov P.V., Golikov A.G.
Synthesis, stereostructure, and biological activity of N-hydroxyoxyalkyl-substituted perhydroquinolines and acridines

344

Krivonogov V.P., Tolstikov G.A., Kozlova G.G., Sivkova G.A., Lazareva D.N., Murinov Yu.I., Zarudii F.S., Myshkin V.A., Ismagilova A.F., Spirikhin L.V., Abdrakhmanov I.B.
Synthesis and biological activity of pyrimidine derivatives

348

Kruglenko V.P., Povstyanoi V.M., Povstyanoi M.V., Kluev N.A.
Reactions of substituted 1,2-diaminoimidazoles with 1,3-dinucleophilic reagents

353

Krukovskaya N.V., Khutoretskii V.M.
Search for information on biologically active dyes containing nitrogeneous heterocycles

356

Kurbatov S.V., Voronina V.A., Olekhnovich L.P.
Dipolar spiroheterocycles containing a superelectrophilic fragment

357

Lakhvich F.A., Koroleva E.V., Pashkovskii F.S.
Modified prostaglandins containing heterocyclic fragments in the w -chain: Synthesis and biological activity

362

Levinson F.S., Efimov S.I., Evgen'ev M.I., Ermolaeva E.A., Falyakhov I.F.
Synthesis of substituted benzodifurazans

364

Makarevich I.F., Gubin Y.I., Georgievskii V.P.
Synthesis of new bioactive compounds from alkaloids and N-heterocyclic cardenolides, bufadienolides, and flavones

370

Mamaeva E.A., Bakibaev A.A., Akhmedzhanov R.R.
New reactions of 7-chloro-1,3-dihydro-3-hydroxy-5-phenyl- 2H-1,4-benzodiazepine-2-one with [bis(acyloxy)iodo]benzene in polar organic solvents

376

Maslivets A.N., Krasnykh O.P., Konyukhova N.A.
2,3-Dihydro-2,3-pyrrolediones in synthesis of azaheterocycles

381

Mel'nikova S.F., Pirogov S.V., Sergievskii A.V., Shaposhnikov S.D., Tselinskii I.V.
1,2,5-Oxadiazole derivatives in synthesis of novel polyheterocyclic systems as potential biologically active compounds

388

Mikhailovskii L.G., Syropyatov B.Ya., Dolzhenko L.V., Shklyaev V.S.
Target synthesis and cardiovascular activity of isoquinoline and phenanthridine derivatives

393

Mironov V.F., Burnaeva L.M., Ivkova G.A., Romanov S.V., Konovalova I.V., Gubaidullin A.T., Litvinov I.A.
New P,N-containing heterocycles through reaction of 2-R-4-oxo-5,6-benzo-1,3,2-dioxaphosphorinanes with imines

398

Mirzaev Yu.R., Shakirov R.Sh., Shakirova U.T.
T-nor,D-homosteroid alkaloids from Veratrum, Korolkowia, and Petilium in fundamental pharmacology

404

Neilands O.
The use of N-carboxymethylazinium and diazolium salts in synthesis of indan-1,3-dione 2-onium derivatives

410

Noritsina M.V., Klochkova I.N., Semenova N.N.
Synthesis and antimicrobial activity of pyrrolidyl-containing thiopyranes and thiapyrilium salts

417

Nurkenov O.A., Gazaliev A.M., Bukeeva A., Aubakirova A., Turdybekov K.M., Kasenov R.Z., Turgunova A.
Derivatives of ephedrine ­lk­l■ids: Synthesis and intramolecular heterocyclyzation

420

Orlov V.Yu., Kotov A.D., Begunov R.S., Mironov G.S.
Aromatic nucleophilic substitution in synthesis and modification of nitrogen-containing heterocycles: A general concept

424

Osadchii S.A., Ganbaatar J., Shults E.E., Tolstikov G.A.
Alkaloids of some Siberian Aconitum and Delphinium species and their modifications

430

Parkhomenko P.I., Makarenko A.G., Musienko +.L., Parkhomenko V.I., Kril' L.M., Kuril'chik S.N.
Heterocyclic nitrogen-containing thiolane- and thiolene-1,1-dioxides: Synthesis, properties, and biological activity

433

Paronikyan E.G., Sirakanyan S.N., Noravyan A.S.
Derivatives of pyrano(thiopyrano)/3,4-Ş/pyridines and 2,7-naphthiridines: Synthesis, transformations, and biological activity

441

Petrov M.L., Abramov M.A., Abramova I.P., Androsov D.A., Dehaen W.
4-(o-Hydroxyaryl)-1,2,3-thia- and selenadiazoles as potential regulators of plant growth: Synthesis and reactivity

449

Praliev K.D., Yu V.K., Poplavskaya I.L.
Target synthesis of pharmacologically active derivatives of 4-ethynyl-4-hydroxypiperidine

454

Razzakov N., Khuzhaev V.U., Aripova S.F., Vakhabov A., Mirzaev Yu.R.
Mono- and dimeric tropane alkaloids from plants of Convolvulus, Datura, and Mandragora species: Pharmacological activity

458

Reznikov V.A., Roshchupkina G.I.
Nucleophilic substitution in halo-substituted enaminones and enhydroxylaminoketones, derivatives of imidazolidine and pyrroline

463

Rubinov D.B., Budnikova M.V., Zheldakova O.A., Mikhal'chuk A.L.
Synthesis of steroid N,S-diheteroanalogs by annelation of cyclic Schiff bases with acylthiocyclanediones

470

Saidkhodzhaeva Sh. A., Usmanova S.K., Bessonova I.A., Dzhakhangirov F.N.
Diterpenoid alkaloids of cultivated and wild Aconitum and Delphinium species

475

Salimov B.T, Dzhakhangirov F.N., Yunusov M.S.
Alkaloids from plants of Delphinium genus and their biological activity

480

Samsonov V.A.
Formation of pyrroline-N-oxide cycle in reaction of a - isonitrosoketone derivatives with enamines and some reactions of obtained compounds

484

Shakirov R.Sh., Shakirova U.T.
Alkaloids of Petilium plants

488

Sharifkanov A.Sh., Alimzhanova S.K., Abilov Zh.A., Bektibaeva A.A., Akhmetbekuly E.
Synthesis of 2,5-dimethyl-1-(pyridin-2-yl-ethyl- and pyridin-4-yl-ethyl)-piperidin-4-ones and some their derivatives

493

Shikhaliev Kh.S., Falaleev A.V., Kryl'skii D.W., Solov'ev A.S.
Hetarylguanidines in reactions of heterocyclization

498

Shklyaev Yu.V., Glushkov V.A., Nifontov Yu.V., Ausheva O.G.
Derivatives of 1-substituted 3,4-dihydroisoquinolines: Synthesis and properties

504

Shvartsberg M.S., Ivanchikova I.D., Barabanov I.I.
Cyclocondensation of acetylenic quinone derivatives with hydrazine

509

Silin A.V., Nikitchenko V.M., Gorobets N.Yu., Borisov A.V., Chuev V.P.
Synthesis of heterocyclic compounds from 2-iminocoumarin

513

Sirakanyan S.N., Paronikyan E.G., Noravyan A.S.
New condensed bioactive derivatives of pyrano[3,4-c]pyridines and 5,6,7,8-tetrahydroisoquinolines

519

Tikhonov A.Ya.
Nitrogenous heterocycles based on a - and b -hydroxylamino oximes

522

Tolmachev A.A.
Direct C-phosphorylation of heterocycles with phosphorus(III) halides

527

Trishin Yu.G., Namestnikov V.I., Tamm L.A., Bel'skii V.K.
Synthesis of P,N-containing bi- and tricyclic compounds by reaction of cyclic trivalent phosphorus derivatives with nitrilimines

532

Tumkevicius S., Kaminskas L., Sarakauskaite Z., I­sevicius V.
peri-Fused heterocycles from 4,5-disubstituted pyrrolo- and thienopyrimidines

538

Tyurina L.A., Kolbin A.M., Valitov R.B.
Azole derivatives in structureÍactivity studies and molecular design of bioactive compounds

541

Ukhin L.Yu., Suponitskii K.Yu., Kartsev V.G.
Modification of cotarnine: Alkylation of cotarnine chloride with organoacetylides of Ag(I) and Cu(I)

543

Velezheva V.S., Gedz' D.E., Gusev D.V., Peregudov A.S., Lokshin B.V., Klemenkova Z.S.
2-Arylidene-3-indolinones in synthesis of indole heterocycles and 4-quinolones

546

Volkova T.D., Nemova N.N.
Styryl derivatives of quinolines and pyridine: Biological action on the cells of tumor lines in vitro

553

Zvonok A.M., Makriyannis A.
Towards the synthesis of azacannabimimetic compounds

557

Author index

561-564

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CONTENTS
VOLUME 2

Poster presentations

5-360

100 selected methods for synthesis and modification of heterocycles

361-462

Author index

463-472



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