SYNTHESIS OF SUBSTITUTED INDOLIZINO[8,7-<i>b</i>]INDOLES FROM HARMINE AND THEIR BIOLOGICAL ACTIVITY

Authors

  • Ж. С. Нурмаганбетов International Research and Production Holding "Phytochemistry", Karaganda 100009
  • Э. Э. Шульц Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • С. В. Чернов Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • А. Ж. Турмухамбетов International Research and Production Holding "Phytochemistry", Karaganda 100009
  • Р. Б. Сейдахметова International Research and Production Holding "Phytochemistry", Karaganda 100009
  • М. М. Шакиров Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • Г. А. Толстиков Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • С. М. Адекенов International Research and Production Holding "Phytochemistry", Karaganda 100009

DOI:

https://doi.org/10.1007/6207

Keywords:

harmine, phenacyl bromides, antimicrobial, cytotoxic, and anticholinesterase activities, acetylation, cyclization, formylation

Abstract

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.

How to Cite
Nurmaganbetov, Zh. S.; Shultz, E. E.; Chernov, S. V.;  Turmukhambetov, A. Zh.; Seydakhmetova, R. B.; Shakirov, M. M.; Tolstikov, G. A.; Adekenov, S. M. Chem. Heterocycl. Compd. 2011, 46, 1494. [Khim. Geterotsikl. Soedin. 2010, 1849.]

For this article in the English edition see DOI 10.1007/s10593-011-0698-z

 

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Published

2021-03-23

Issue

No. 12 (2010)

Section

Original Papers