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Open Chemistry

formerly Central European Journal of Chemistry


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Open Access
Online
ISSN
2391-5420
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Volume 1, Issue 1

Issues

Volume 13 (2015)

Synthesis of vinca alkaloids and related compounds 991. A new heterocyclic system

Pál Csókási
  • Institute of Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, H-1525, POB 17, Budapest, Hungary
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/ Eszter Gács-Baitz
  • Institute of Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, H-1525, POB 17, Budapest, Hungary
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/ Csaba Szántay
  • Institute of Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, H-1525, POB 17, Budapest, Hungary
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Published Online: 2003-03-01 | DOI: https://doi.org/10.2478/BF02479258

Abstract

Utilising our earlier intermediate obtained by the umpolung reactivity of quinolizidine enamines, a new heterocyclic system: (11bSR, 15aSR)-1,2,3,6,11,14,15,15a-Octahydro-5H-indolo [2′,3′:3,4]pyrido[2,1-j]-1,6-naphthyridin-13(12H)-one was synthesised and its biological effects evaluated. Although modest, significant and selective effects were detected.

Keywords: alkaloids; stereochemistry; cyclization; new ring system; indolo[2,3-a]quino-lizidines

  • [1] J. Éles, Gy. Kalaus, A. Lévai, I. Greiner, M. Kajtár-Peredy, P. Szabó, L. Szabó and Cs. Szántay: “Synthesis of vinca alkaloids and related compounds 98. Oxidation with dimethoxyoxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7S,20S)-(+)-Rhaizidigenine and (2R, 7S, 20S)-(+)-rhaizidine”, J. Heterocyclic Chem., Vol. 39, (2002), pp. 767–771. Google Scholar

  • [2] A. Lukács, L. Szabó, E. Baitz-Gács, P. Bombicz, A. Dobó, Gy. Kalaus and Cs. Szántay: “Umpolung reactions of enamines through enamonium salts”, Heterocycles, Vol. 48, (1998), pp. 2507–2520. http://dx.doi.org/10.3987/COM-98-8266CrossrefGoogle Scholar

  • [3] J. Sápi, L. Szabó, E. Baitz-Gács, Gy. Kalaus and Cs. Szántay: “Synthesis of vinca alkaloids and related compounds XLII. Transformation of vincamone into vincamines via diazomethane assisted homologization. Application of 1H-NOE measurements for the configurational assignment of the spiro-oxirane ring”, Tetrahedron, Vol. 44, (1988), pp. 4619–4629. http://dx.doi.org/10.1016/S0040-4020(01)86164-0CrossrefGoogle Scholar

About the article

Published Online: 2003-03-01

Published in Print: 2003-03-01


Citation Information: Open Chemistry, Volume 1, Issue 1, Pages 65–68, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/BF02479258.

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© 2003 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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