Advertisement

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
Article

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.

Keywords

harmine phenacyl bromides antimicrobial cytotoxic and anticholinesterase activities acetylation cyclization formylation 

References

  1. 1.
    Y. Toyoda, H. Kumagai, H. Irikawa, and Y. Okumura, Chem. Lett., 903 (1982).Google Scholar
  2. 2.
    T.-S. Kan and K. M. Sin, Phytochemistry, 47, 145 (1998).CrossRefGoogle Scholar
  3. 3.
    Y. Liu, S. Luo, X. Fu, F. Fang, Z. Zhuang, W. Xiong, X. Jia, and H. Zhai, Org. Lett., 8, 115 (2006).CrossRefGoogle Scholar
  4. 4.
    J. Kobayashi, M. Sekiguchi, S. Shimamoto, H. Shigemori, H. Ishiyama, and A. Ohsaki, J. Org. Chem., 67, 6449 (2002).CrossRefGoogle Scholar
  5. 5.
    M. T. Agedilova, A. Zh. Turmukhambetov, A. V. Kazantsev, E. E. Shultz, M. M. Shakirov, and S. M. Adekenov, Khim. Prirod. Soed., 186 (2006).Google Scholar
  6. 6.
    A. Zh. Turmukhambetov, M. T. Agedilova, Zh. S. Nurmaganbetov, A. V. Kazantsev, E. E. Shultz, M. M. Shakirov, I. Yu. Bagryanskaya, and S. M. Adekenov, Khim. Prirod. Soed., 504 (2009).Google Scholar
  7. 7.
    K. Takasu, T. Shimogama, C. Saiin, H.-S. Kim, Y. Wataya, and M. Ihara, Bioorg. Med. Chem. Lett., 14, 1689 (2004).CrossRefGoogle Scholar
  8. 8.
    V. Amendola, M. Biocchi, L. Fabbrizzi, and A. Palchetti, Chem. Eur. J.¸5648 (2005).Google Scholar
  9. 9.
    J. F. Blom, T. Brütsch, D. Barbaras, Y. Bethuel, H. H. Locher, C. Hubschwerlen, and K. Gademann, Org. Lett., 8, 737 (2006).CrossRefGoogle Scholar
  10. 10.
    E. T. Borrows and D. O. Holland, Chem. Rev., 42, 615 (1948).CrossRefGoogle Scholar
  11. 11.
    T. J. Hagen, K. Narayanan, J. Names, and J. M. Cook, J. Org. Chem., 54, 2170 (1989).CrossRefGoogle Scholar
  12. 12.
    C. Chen, C. H. Senanayake, T. J. Bill, R. D. Larsen, T. R. Verhoeven, and P. J. Reider, J. Org. Chem., 59, 3738 (1994).CrossRefGoogle Scholar
  13. 13.
    J. P. Kutney, N. Abdurahman, C. Gletsos, P. Le Quesne, E. Piers, and I. Vlattas, J. Am. Chem. Soc., 92, 1727 (1970).CrossRefGoogle Scholar
  14. 14.
    S. Iwadare, Y. Shizuri, K. Yamada, and Y. Hirata, Tetrahedron, 34, 1457 (1978).CrossRefGoogle Scholar
  15. 15.
    V. S. Giri, S. K. Das, P. J. Sankar, J. N. Shoolery, and P. Keifer, J. Heterocycl. Chem., 29, 767 (1992).CrossRefGoogle Scholar
  16. 16.
    V. S. Giri, B. C. Maiti, S. B. Mandal, and S. C. Pakrashi, J. Chem. Res., Synop., 342 (1988).Google Scholar
  17. 17.
    G. Poissonnet, M.-H. Theret-Bettiol, and R. H. Dodd, J. Org. Chem., 61, 2273 (1996).CrossRefGoogle Scholar
  18. 18.
    J. Ishida, H. K. Wang, K. F. Bastow, C. Q. Hu, and K. H. Lee, Bioorg. Med. Chem. Lett., 9, 3319 (1999).CrossRefGoogle Scholar
  19. 19.
    T. E. Shaikenov, S. M. Adekenov, R. M. Williams, and F. L. Baker, Life Sci., 70, 49 (2001).CrossRefGoogle Scholar
  20. 20.
    M. Heinrich and H. L. Teoh, Ethnopharmacol., 92, 147 (2004).CrossRefGoogle Scholar
  21. 21.
    M. Dekhane, L. Dubois, G. Blanchet, H. Garrigue, H. Sentenac-Roumanou, P. Potier, and R. H. Dodd, Bioorg. Med. Chem. Lett., 3, 2831 (1993).CrossRefGoogle Scholar

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

Personalised recommendations