Chemistry of Heterocyclic Compounds

, Volume 46, Issue 12, pp 1494–1499 | Cite as

Synthesis of substituted indolizino[8,7-b]indoles from harmine and their biological activity

  • Zh. S. Nurmaganbetov
  • E. E. Shultz
  • S. V. Chernov
  • A. Zh. Turmukhambetov
  • R. B. Seydakhmetova
  • M. M. Shakirov
  • G. A. Tolstikov
  • S. M. Adekenov

The reaction of harmine with phenacyl bromides or ethyl bromoacetate gives quaternized harmine derivatives. The cyclization of the phenacylharminium salts yields the corresponding 2-aryl-11H-indolizino[8,7-b]indoles. Vilsmaier-Haack formylation of 11H-indolizino[8,7-b]indoles leads to the corresponding 3,10-bisformyl derivatives. The acylation proceeds selectively at C(3) to give 3-acetyl-2-aryl-11H-indolizino[8,7-b]indole.


harmine phenacyl bromides antimicrobial cytotoxic and anticholinesterase activities acetylation cyclization formylation 


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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • Zh. S. Nurmaganbetov
    • 1
  • E. E. Shultz
    • 2
  • S. V. Chernov
    • 2
  • A. Zh. Turmukhambetov
    • 1
  • R. B. Seydakhmetova
    • 1
  • M. M. Shakirov
    • 2
  • G. A. Tolstikov
    • 2
  • S. M. Adekenov
    • 1
  1. 1.International Research and Production Holding “Phytochemistry”KaragandaKazakhstan
  2. 2.Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussia

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