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)

Москва: "Иридиум-пресс", 2001, том 1 - 568 страниц, том 2 - 472 страницы

Настоящее двухтомное издание создано по материалам пленарных, устных и стендовых докладов Первой Международной конференции "Химия и биологическая активность азотистых гетероциклов и алкалоидов", организованной компанией InterBioScreen Ltd., Фондом "Научное партнерство", при участии и поддержке Российской Академии наук, Московского Государственного университета им. М.В. Ломоносова и Комитета по науке и технологиям при Правительстве г. Москвы.

Конференция открывает цикл ежегодных научных форумов "Химия и биологическая активность синтетических и природных соединений", и не случайно первый из них посвящен наиболее объемной и интересной области химии - синтетическим азотистым гетероциклам и их природным представителям - алкалоидам.

Организаторы конференции ставили целью дать возможность встретиться вместе химикам-синтетикам, специалистам по химии природных соединений, медицинским химикам и фармакологам и, таким образом, убрать барьеры дисциплинарной специализации и дать возможность участникам, работающим в различных областях химии биологически активных соединений, обсудить наиболее актуальные вопросы современного состояния этой многогранной области науки.

Учитывая важность научных материалов участников конференции и ее междисциплинарный характер, оргкомитет нашел возможным выйти за рамки издания кратких тезисов и опубликовать научные материалы конференции в виде полноформатных обзоров (пленарные доклады), статей (устные доклады) и кратких сообщений (материалы стендовых сессий). Это привело к появлению настоящего двухтомника, который, надеемся, станет началом периодического издания научных трудов будущих конференций.

Оба тома настоящего издания параллельно выходят на английском языке, что даст возможность широкой мировой научной общественности быть в курсе достижений отечественной науки в данной области.

В последний раздел издания включены описания 100 наиболее интересных методов синтеза и модификации гетероциклов, разработанных учеными СНГ и стран Балтии за последние несколько лет. Материалов в этот раздел пришло столь много, что Фонд "Научное партнерство" принял решение об издании отдельного периодического сборника в промежутке между конференциями.

В.Г. Карцев
Председатель оргкомитета,
Доктор химических наук,
Вице-президент InterBioScreen Ltd.,
Председатель Правления Фонда
"Научное партнерство"

ОГЛАВЛЕНИЕ
ТОМ 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 structureЦactivity 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. StructureЦactivity 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 heterocyclesЧpromising 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 ю-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 рlkрlюids: 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-ё/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., Iрsevicius V. peri-Fused heterocycles from 4,5-disubstituted pyrrolo- and thienopyrimidines	538
Tyurina L.A., Kolbin A.M., Valitov R.B. Azole derivatives in structureЦactivity 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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