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Journal №2 for 2014 г.
Article in number:
Phytodrugs of VILAR at the basis of quinolyzidine, pyrrolyzidine, peptide, monomeric and dimeric isoquinoline alkaloids: chemical and technological study. 2nd Report
Keywords: isoquinoline aporphine indole benzophenanthridine eregot ephedra alkaloids
Authors:
O.N. Tolkachev - Dr.Sc. (Chem.), Professor, Department of Phytochemistry, All-Russian Scientific Research Institute of Medicinal and Aromatic Plants (VILAR). E-mail: vilarnii@mail.ru
O.P. Sheichenko - Ph.D. (Chem.), Head of Department of Phytochemistry, All-Russian Scientific Research Institute of Medicinal and Aromatic Plants (VILAR)
L.V. Krepkova - Ph.D. (Biol.), Head of Toxicology Department, All-Russian Scientific Research Institute of Medicinal and Aromatic Plants (VILAR). E-mail: krepkowa2011@yandex.ru
T.A. Savina - Ph.D. (Biol.), Head of Laboratory of Biotechnology, All-Russian Scientific Research Institute of Medicinal and Aromatic Plants (VILAR)
T.A. Sokol-skaya - Dr.Sc. (Pharm.), Professor, Deputy Director, All-Russian Scientific Research Institute of Medicinal and Aromatic Plants (VILAR). E-mail: vilarnii@mail.ru
N.I. Sidel-nikov - Ph.D. (Biol.), Director, All-Russian Scientific Research Institute of Medicinal and Aromatic Plants (VILAR). E-mail: vilarnii@mail.ru
Abstract:
Brief overview on the chemical, analytical, technological, biotechnological study of the alkaloid containing plants and individual alkaloids with references on medico-biological, toxicological, clinical and agrochemical aspects in GNU VILAR after 1970, which summarized: isolation, chemical structure elucidation, chemical transformation, analytical and technological aspects. The plant alkaloids of the isoqinoline, bisbenzylisoquinoline, quinolyzidine, pyrrolizidine, phenylethanolamine etc. series their derivatives produced from Claviceps, Hypecoum, Stephania etc., their properties, chemical transformations, the drugs on their basis, and the prospects of their uses in medicine were presented in the second issue. Some results of toxicological and clinical studies were also discussed.
Pages: 4-19
References

 

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  71. Murav'eva D.A., Tolkachev O.N., Akopov A.A. Alkaloidy' nadzemnoj chasti Thalictrum minus i Th. fetidum // Ximiya prirodny'x soedinenij. 1985. № 3. S. 416 - 417.
  72. Abizov E.A., Tolkachev O.N. Dinamika nakopleniya i raspredelenie β-karbolinovy'x alkaloidov u vidov roda lox, introduczirovanny'x v Moskovskoj oblasti // Ximiko-farmaczevti-cheskij zhurnal. 2011. T. 43, № 10. S. 42 - 43.
  73. Tolkachev O.N., Nakova E.P., Vukolova A.I., Aranovich G.I., Evstigneeva R.P. Issledovanie enaminotioe'firov. Sintez zameshhenny'x amidov ariluksusny'x kislot // Zhurnal obshhej ximii. 1974. T. 44(2). S. 410 - 414.
  74. Nakova E.P., Tolkachev O.N., Evstigneeva R.P. Reaction of primary amines with substituted acetophenones and sulphur // IInd Symposium with International Participation on Structure and Reactivity of Organic Compounds. Sept. 29 - Oct. 2, 1975. Slanchev Bryag, Burgas, Bulgaria. Manuscripts of Contributed Papers. № 42, P. 45.
  75. Nakova E.P., Tolkachev O.N., Evstigneeva R.P. Synthesis of substituted 1-benzyl-3,4-dihydroisoquinolines from enaminothioethers // IInd Symposium with International Participation on Structure and Reactivity of Organic Compounds. Sept.29 Oct.2, 1975. Slanchev Bryag, Burgas, Bulgaria. Manuscrips of Contributed Papers. № 110. P. 124.
  76. Nakova E.P., Tolkachev O.N., Evstigneeva R.P. Sintez N-zameshhenny'x tioamidov iz pervichny'x aminov po reakczii Vil'gerodta-Kindlera // Zhurnal organicheskoj ximii, 1975. T. 11. № 12. S. 2585 - 2589.
  77. A.s. № 550386. Sposob polucheniya zameshhenny'x 1-benzil-3,4-digidroizoxinolinov / E.P. Nakova, O.N. Tolkachev, R.P. Evstigneeva.
  78. Tolkachev O.N., Nakova E.P., Evstigneeva R.P. Application of the Wilgerodt-Kindler Reaction in the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids and their derivatives // IUPAC 11th International Symposium on the Chemistry of Natural Products. Symposium papers. V.3. Synthesis of natural products. Golden Sands, Bulgaria. Sept. 17-23, 1978. Bulg. Acad. Sci. Sofia. P. 47 ? 50; C.A., 92, 129139t (1980).
  79. Tolkachev O.N., Nakova E.P., Evstigneeva R.P. Sintez 1-benzilizoxinolinovy'x alkaloidov i ix proizvodny'x cherez N-arile'tilariltioaczetamidy' // Tezisy' dokl. V Sovetsko-indijskogo simp. po ximii prirodny'x soedinenij. Erevan. 11-17 maya 1978. S. 63.
  80. Nakova E.P., Tolkachev O.N., Evstigneeva R.P. Sintez N-arile'tilariltioaczetamidov po reakczii Vil'gerodta-Kindlera i ix prevrashhenie v zameshhenny'e 1-benzil-1,2,3,4-tetragidroizoxinoliny' // Zhurnal organicheskoj ximii. 1981. T. 17. № 3. S. 637 - 642.
  81. A.s. № 1540231 (SSSR). Sposob polucheniya proizvodny'x 3-aminoizoxinolina / A.V. Sereda, O.N. Tolkachev, B.M. Zolotarev, I.V. Jarczeva.
  82. A.s. № 1616083 (SSSR). Proizvodny'e 3-amino-6,7-dimetoksiizoxinolina, obladayushhie spazmoliticheskoj aktivnost'yu / A.V. Sereda, S.Ja. Sokolov, L.F. Belova, O.N. Tolkachev.
  83. Sereda A.V., Sukhov I.E., Zolotarev B.M., Yartseva I.V., Tolkachev O.N. Acid promoted cyclocondensation of nitriles. Part I. Novel synthesis of 3-aminoisoquinolines and their derivatives // Tetrahedron Letters. 1992. V. 33. № 29. P. 4205 - 4208.
  84. Sereda A.V., Tolkachev O.N. Novy'e biologicheski aktivny'e proizvodny'e papaverina // Tezisy' dokl. nauch.-prakt. konf. «Perspektivy' sozdaniya i proizvodstva lekarstvenny'x sredstv v Ukraine».
  85. Sereda A.V., Suxov I.E., Lapa G.B., Zolotarev B.M., Jarczeva I.V., Tolkachev O.N. Kislotnokataliziruemaya cziklokondensacziya nitrilov. II. Novy'j sintez 3-aminoizoxinolinov, 3-imidoilaminoizoxinolinov i 3-imino-2-azaspiro[4,5]deka-6,9-dien-8-ona // Zhurnal organicheskoj ximii. 1994. T. 30. № 12. S. 1782 - 1790.
  86. Lapa G.B., Tolkachev V.O., Ivanova T.P., Tolkachev O.N. Kislotokataliziruemaya cziklokondensacziya nitrilov. III. Sintez zameshhenny'x 3-aminoizoxinolinov i ix czitotoksicheskaya aktivnost' // Ximiko-farmaczevticheskij zhurnal. 1996. T. 30(1). S. 16 - 18.
  87. Sereda A.V., Sukhov I.E., Lapa G.B., Tolkachev O.N. Acid promoted cyclocondensation of arylacetonitriles // 10th International conference on organic synthesis (ICOS-10). Dec. 11-16, 1994. Bangalore, India. Abstracts. P. 179, P-WED-99.
  88. Sereda A.V., Tolkachev O.N. Synthesis of new Troeger bases from 3-aminoisoquinolines // 15th International Congress of Heterocyclic Chemistry. Taipei. August 6 - 11, 1995. Abstracts, PO2 - 210.
  89. Sereda A.V., Lapa G.B., Suxov I.E., Belova L.F., Sokolov S.Ja., Miroshnikov A.I., Tolkachev O.N. Kislotokataliziruemaya cziklokondensacziya nitrilov. IV. Sintez i spazmoliticheskaya aktivnost' 1-zameshhenny'x 3-aminoizoxinolinov // Ximiko-farmaczevticheskij zhurnal. 1997. T. 31. № 4. C. 22 - 27.
  90. Tolkachev V.N., Skurydina D.F., Nikolaeva T.G., Sereda A.V., Sukhov I.E., Lapa G.B., Tolkachev O.N. Structure - Antitumor activity study of polyoxigenated indoles and isoquinolines // XVIth International Cancer Congress. Oct. 30 - Nov. 5, 1994. New-Delhi, India. Abstracts. Book-1, PSB 11 - 15. P. 303.
  91. Sheth J.P., Tolkachev O.N. An approach to the synthesis of racemic O,O?-dimethyl isochondodendrine // Tetrahedron Letters. 1967. V. 8. № 13. P. 1161 - 1163.
  92. Tolkachev O.N. Synthetic investigation of curare Alkaloids // J. Sci. & Industr. Res. 1967. V. 26. № 5. P. 209 - 212.
  93. Volkova L.V., Kosmacheva V.E., Voronin V.G., Tolkachev O.N., Preobrazhenskij N.A. Sinteticheskie issledovaniya v oblasti kurarealkaloidov. XIX. Sintez dimetilovogo e'fira raczemicheskogo lienzinina // Ximiya geterocziklich. soedinenij. 1967. № 3. S. 522 - 526.
  94. Voronin V.G., Tolkachev O.N., Proxorov A.B., Chernova V.P., Preobrazhenskij N.A. Sinteticheskie issledovaniya v oblasti kurarealkaloidov. XIII. Cintez izomerny'x tubokurarin-iodidov // Ximiya geterocziklich. soedinenij, 1969. № 4. S. 606 - 610.
  95. A.s. № 554674. Sposob polucheniya (()-O-metildauriczina / E.P. Nakova, O.N. Tolkachev, R.P. Evstigneeva.
  96. Tolkachev O.N., Nakova E.P., Evstigneeva R.P. Bisbenzilizoxinolinovy'e alkaloidy' // Ximiya prirodny'x soedinenij. 1977. № 4. S. 451 - 484.
  97. Tolkachev O.N., Jaxontova L.D., Romanenko E.A., Firsova G.A., Mazaeva V.G., Sedakova L.A. Rezul'taty' predvaritel'nogo izucheniya protivoopuxolevoj aktivnosti monoe'firny'x bisbenzilizoxinolinovy'x alkaloidov ryada magnolina-magnolamina // Sb. «Ximioterapiya opuxolej v SSSR». 1977. Vy'p. 23-24. ONC AMN SSSR, M. S. 117 - 121.
  98. Tolkachev O.N., Vichkanova S.A., Makarova L.V., Najdovich L.P. Zavisimost' tuberkulostaticheskoj aktivnosti bisbenzilizoxinolinovy'x alkaloidov ot ix struktury' // Farmacziya. 1978. T. 27(2). S. 23 - 26.
  99. Tolkachev O.N., Yakhontova L.D., Ronanenko E.A., Firsova G.A., Mazaeva V.G., Sedakova L.A., Sof-ina Z.P. The structure ? antitumor activity of some bisbenzylisoquinoline alkaloids / In: Consultation on Potentials for Use of Plants Indicated by Traditional Medicine in Cancer Therapy. WHO. Geneva. 13-17 November 1978. WP 7 (7 P.).
  100. Tolkachev O.N., Jaxontova L.D., Romanenko E.A., Firsova G.A., Mazaeva V.G., Sedakova L.A., Sof'ina Z.P. Protivoopuxolevaya aktivnost' nekotory'x bifunkczional'ny'x alkaloidov i ix proizvodny'x // Tezisy' dokl. Vses. nauch. konf. «Sintez i izuchenie novy'x otechestvenny'x protivolejkozny'x preparatov». Vil'nyus. 1979. S. 81.
  101. Tolkachev O.N., Sheichenko O.P., Sheichenko V.I. Stereostructure and electrophyllic reaction of cycleanine // IUPAC 12th International Symposium on the Chemistry of Natural Products. Sept. 21 - 27 1980. Puerto de la Crus. Tenerife, Canary Islands. Spains. Abstracts. 1980. B90.
  102. Tolkachev O.N., Nakova E.P., Evstigneeva R.P. Sintez bisbenzilizoxinolinovy'x alkaloidov // Uspexi ximii. 1980. T. 49. № 8. S. 1617 - 1647.
  103. Shejchenko O.P., Tolkachev O.N. Reakcziya termoliza i fotoliza czikleanina // Ximiya prirodny'x soedinenij. 1980. № 2. S. 263 - 264.
  104. Nakova E.P., Tolkachev O.N. Application of cyclobiscondensation of enaminothioethers with phenethylamines in the synthesis of bisbenzylisoquinoline alkaloids // F.E.C.S. - First International Conference on Chemistry and Biotechnology of Biologically Active Natural Products. Varna, Bulgaria. 21 - 26. 09.1981. Short Communications. «Syntheses and Enzymatic Transformations and Biosyntheses». V. 3. № 2. P. 26 - 31; C.A., 97, 92607 (1982).
  105. Nakova E.P., Tolkachev O.N. The Willgerodt-Kindler Cyclobisaddition Reaction in the Synthesis of Stebisimine, (()-Obaberine and (()-Isotetrandrine // F.E.C.S. First International Sonference on Chemistry and Biotechnology of Biologically Active Natural Products. Varna, Bulgaria. 21 - 26. 09.1981. Short Communications. «Syntheses and Enzymatic Transformations and Biosyntheses». V. 3. № 2. P. 32 - 36; C.A., 97, 127862 (1982).
  106. Nakova E.P., Tolkachev O.N., Evstigneeva R.P. Novel synthesis of O-methyldauricine // F.E.C.S. - First International Sonference on Chemistry and Biotechnology of Biologically Active Natural Products. Varna, Bulgaria. 21 - 26. 09.1981. Short Communications. «Syntheses and Enzymatic Transformations and Biosyntheses». V. 3. № 2. P. 570 - 573; C.A., 97, 110246 (1982).
  107. A.s. № 36547(NRB). Sposob polucheniya bisbenzilizoxinolinov (na osnove enaminotioe'firov) / E.P. Nakova, O.N. Tolkachev.
  108. A.s. 36549 (NRB). Ciklobistioamidy' i sposob polucheniya poslednix / E.P. Nakova, O.N. Tolkachev.
  109. A.s. № 36550 (NRB) Sposob polucheniya bisbenzilizoxinolinov (na osnove cziklobistioamidov) / E.P. Nakova, O.N. Tolkachev.
  110. Tolkachev O.N., Monaxova T.E., Shejchenko O.P., Shejchenko V.I. Termicheskoe O-demetilirovanie alkaloidov izoxinolinovogo ryada // Tezisy' dokl. III Moskovskaya konf. po organicheskoj ximii i texnologii. 20 - 22.10.1982. M. VXO im. D.I. Mendeleeva. Moskovskoe pravlenie. Sekcziya organicheskoj ximii. 1982. S. 110.
  111. Sheichenko V.I., Sheichenko O.P., Tolkachev O.N. A solvent effect upon the methylimino group configuration in the isochondodendrine type alkaloids // IUPAC 14th International Symposium on the Chemistry of Natural Products. July 09 - 14 1984. Poznan, Poland. Abstracts I A 61. P. 175.
  112. A.s. № 1170660. Sposob polucheniya czikleanina / O.P. Shejchenko, I.I. Fadeeva, O.N. Tolkachev.
  113. Nakova E.P., Tolkachev O.N. Novy'j sintez stebisimina, (()-obaberina i (()-izotetrandrina na osnove enaminotioe'firov. I // Ximiya prirodny'x soedinenij. 1985. № 1. S. 86 - 91.
  114. Nakova E.P., Tolkachev O.N. Cintez stebisimina, (()-obaberina i (()-izotetrandrina na osnove cziklobiskondensaczii Vil'gerodta-Kindlera. II // Ximiya prirodny'x soedinenij. 1985. № 1. S. 91 ? 95.
  115. Tolkachev O.N. K strukture makrocziklicheskix tautomerny'x bis-(1-benzildigidroizoxinolinov) // Ximiya, texnologiya, mediczina. Trudy' VILAR, M. 2003. T. XVI. S. 107 - 111.
  116. Shejchenko O.P., Tolkachev O.N. N-Okisi czikleanina // Sb. nauch. trudov «Ximicheskaya i mediko-biologicheskaya oczenka novy'x fitopreparatov». VILR. M. 1989. S. 23 - 24.
  117. Nakova E.P., Tolkachev O.N., Evstigneeva R.P. Novy'j sintez (()-O-metildauriczina // Ximiya prirodny'x soedinenij. 1981. № 4. S. 457 - 460.
  118. Tolkachev O.N., Shreter A.I. Rol' stereoximicheskix priznakov v xemotaksonomicheskom izuchenii rastenij // Rastitel'ny'e resursy'. 1979. T. 15. № 3. S. 321 - 343.
  119. Tolkachev O.N., Firsova G.A., Mazaeva V.G., Sedakova L.A., Romanenko E.A. Structure - Activity relationship study of the bisbenzylisoquinoline alkaloids // 9th NCI-EORT Symposium on New Drugs in Cancer Therapy. Amsterdam, Netherland. March 12 - 15, 1996. in: «Drug design, synthesis, acquisition and structure activity relationships». Downloaded from annonc. Oxford Journals Org. at State Public Library for Science and Technology on May 29. 2010. (379). P. 108.