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Russian Chemical Bulletin

, Volume 67, Issue 11, pp 2103–2107 | Cite as

Synthesis and biological activity of 5-vinyl- and 5-allyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles

  • V. B. Sokolov
  • A. Yu. AksinenkoEmail author
  • T. A. Epishina
  • T. V. Goreva
  • E. F. Shevtsova
  • L. G. Dubova
  • P. N. Shevtsov
  • E. V. Rudakova
  • N. V. Kovaleva
  • G. F. Makhaeva
  • S. O. Bachurin
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Abstract

A synthetic approach to the vinylation and allylation of tetrahydro-γ-carbolines with alkane dimethyl sulfonates in the presence of sodium hydride was developed. The effect of the synthesized 5-vinyl- and 5-allyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles on acetylcholinesterase, butyrylcholinesterase, and carboxylesterase activity, mitochondrial functions, and tubulin polymerization was investigated, and their antioxidant activity was evaluated.

Key words

tetrahydro-γ-carbolines alkane dimethyl sulfonates sodium hydride vinylation butyrylcholinesterase antioxidants mitoprotectors 

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References

  1. 1.
    S. O. Bachurin, E. V. Bovina, A. A. Ustyugov, Med. Res. Rev., 2017, 37, 1186.CrossRefGoogle Scholar
  2. 2.
    S. O. Bachurin, S. I. Gavrilova, A. Samsonova, G. E. Barreto, G. Aliev, Pharmacol. Res., 2018, 129, 216.CrossRefGoogle Scholar
  3. 3.
    O. B. Smirnova, T. V. Golovko, V. G. Granik, Pharm. Chem. J., 2011, 44, 654; DOI: 10.1007/s11094-011-0540-z.CrossRefGoogle Scholar
  4. 4.
    O. M. Peters, N. Connor-Robson, V. B. Sokolov, A. Yu. Aksinenko, M. S. Kukharsky, S. O. Bachurin, N. N. Ninkina, V. L. Buchman, J. Alzheimer’s Dis., 2013, 33, 1041.CrossRefGoogle Scholar
  5. 5.
    S. O. Bachurin, A. A. Ustyugov, N. N. Ninkina, V. B. Sokolov, A. Yu. Aksinenko, T. A. Shelkovnikova, A. V. Bolkunov, Pat. RF 2490268, 2013 (in Russian).Google Scholar
  6. 6.
    V. B. Sokolov, A. Yu. Aksinenko, S. O. Bachurin, Russ. J. Gen. Chem., 2014, 84, 1694.CrossRefGoogle Scholar
  7. 7.
    V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, V. V. Grigoriev, A. V. Gabrelґyan, S. O. Bachurin, Russ. Chem. Bull., 2015, 64, 718.CrossRefGoogle Scholar
  8. 8.
    G. F. Makhaeva, S. V. Lushchekina, N. P. Boltneva, V. B. Sokolov, V. V. Grigoriev, O. G. Serebryakova, E. A. Vikhareva, A. Yu. Aksinenko, G. E. Barreto, S. O. Bachurin, G. Aliev, Sci. Rep., 2015, 5, 13164.CrossRefGoogle Scholar
  9. 9.
    S. O. Bachurin, E. F. Shevtsova, G. F. Makhaeva, V. V. Grigoriev, N. P. Boltneva, N. V. Kovaleva, S. V. Lushchekina, P. N. Shevtsov, M. E. Neganova, O. M. Redkozubova, E. V. Bovina, A. V. Gabrelyan, V. P. Fisenko, V. B. Sokolov, A. Yu. Aksinenko, V. Echeverria, G. E. Barreto, G. Aliev, Sci Rep., 2017, 7, 45627.CrossRefGoogle Scholar
  10. 10.
    V. B. Sokolov, G. F. Makhaeva, A. Yu. Aksinenko, V. V. Grigoriev, E. F. Shevtsova, S. O. Bachurin, Russ. Chem. Bull., 2017, 66, 1821.CrossRefGoogle Scholar
  11. 11.
    V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, Russ. J. Gen. Chem., 2017, 87.Google Scholar
  12. 12.
    A. Y. Lebedev, V. V. Izmer, D. N. Kazyul’kin, I. P. Beletskaya, A. Z. Voskoboynikov, Org. Lett., 2002, 4, 623.CrossRefGoogle Scholar
  13. 13.
    B. A. Trofimov, R. N. Nesterenko, A. I. Mikhaleva, A. B. Shapiro, I. A. Aliev, I. V. Yakovleva, G. A. Kalabin, Chem. Heterocycl. Compd., 1986, 22, 393.CrossRefGoogle Scholar
  14. 14.
    A. V. Ivachtchenko, E. B. Frolov, O. D. Mitkin, S. E. Tkachenko, M. I. Okun, A. V. Khvat, Bioorg. Med. Chem. Lett., 2010, 20, 78.CrossRefGoogle Scholar
  15. 15.
    N. K. Kochetkov, N. F. Kucherova, I. G. Zhukova, J. Gen. Chem. USSR, 1961, 31, 853.Google Scholar
  16. 16.
    J. Poldy, R. Peakal, R. A. Barrow, Tetrahedron Lett., 2008, 49, 2446.CrossRefGoogle Scholar
  17. 17.
    G. F. Makhaeva, V. B. Sokolov, E. F. Shevtsova, N. V. Kovaleva, S. V. Lushchekina, N. P. Boltneva, E. V. Rudakova, A. Yu. Aksinenko, P. N. Shevtsov, M. E. Neganova, L. G. Dubova, S. O. Bachurin, Pure Appl. Chem., 2017, 89, 1167.CrossRefGoogle Scholar
  18. 18.
    R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Rad. Biol. Med., 1999, 26, 1231.CrossRefGoogle Scholar
  19. 19.
    G. F. Makhaeva, S. V. Lushchekina, N. P. Boltneva, O. G. Serebryakova, E. V. Rudakova, A. A. Ustyugov, S. O. Bachurin, A. V. Shchepochkin, O. N. Chupakhin, V. N. Charushin, R. J. Richardson, Bioorg. Med. Chem., 2017, 25, 5981.CrossRefGoogle Scholar
  20. 20.
    S. G. Klochkov, M. E. Neganova, S. V. Afanas’eva, E. F. Shevtsova, Pharm. Chem. J., 2014, 48, 15; DOI: 10.1007/s11094-014-1035-5.CrossRefGoogle Scholar
  21. 21.
    M. L. Shelanski, F. Gaskin, C. R. Cantor, Proceed. Nation. Acad. Sci. USA, 1973, 70, 765.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • V. B. Sokolov
    • 1
  • A. Yu. Aksinenko
    • 1
    Email author
  • T. A. Epishina
    • 1
  • T. V. Goreva
    • 1
  • E. F. Shevtsova
    • 1
  • L. G. Dubova
    • 1
  • P. N. Shevtsov
    • 1
  • E. V. Rudakova
    • 1
  • N. V. Kovaleva
    • 1
  • G. F. Makhaeva
    • 1
  • S. O. Bachurin
    • 1
  1. 1.Institute of Physiologically Active CompoundsRussian Academy of SciencesChernogolovka, Moscow RegionRussian Federation

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