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

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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.

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References

  1. S. O. Bachurin, E. V. Bovina, A. A. Ustyugov, Med. Res. Rev., 2017, 37, 1186.

    Article  CAS  PubMed  Google Scholar 

  2. S. O. Bachurin, S. I. Gavrilova, A. Samsonova, G. E. Barreto, G. Aliev, Pharmacol. Res., 2018, 129, 216.

    Article  CAS  PubMed  Google Scholar 

  3. O. B. Smirnova, T. V. Golovko, V. G. Granik, Pharm. Chem. J., 2011, 44, 654; DOI: 10.1007/s11094-011-0540-z.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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. V. B. Sokolov, A. Yu. Aksinenko, S. O. Bachurin, Russ. J. Gen. Chem., 2014, 84, 1694.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  11. V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, Russ. J. Gen. Chem., 2017, 87.

    Google Scholar 

  12. A. Y. Lebedev, V. V. Izmer, D. N. Kazyul’kin, I. P. Beletskaya, A. Z. Voskoboynikov, Org. Lett., 2002, 4, 623.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  15. N. K. Kochetkov, N. F. Kucherova, I. G. Zhukova, J. Gen. Chem. USSR, 1961, 31, 853.

    Google Scholar 

  16. J. Poldy, R. Peakal, R. A. Barrow, Tetrahedron Lett., 2008, 49, 2446.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  18. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Rad. Biol. Med., 1999, 26, 1231.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  21. M. L. Shelanski, F. Gaskin, C. R. Cantor, Proceed. Nation. Acad. Sci. USA, 1973, 70, 765.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. B. Sokolov, A. Yu. Aksinenko, 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

Authors
  1. V. B. Sokolov
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  2. A. Yu. Aksinenko
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  3. T. A. Epishina
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  4. T. V. Goreva
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  5. E. F. Shevtsova
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  6. L. G. Dubova
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  7. P. N. Shevtsov
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  8. E. V. Rudakova
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  9. N. V. Kovaleva
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  10. G. F. Makhaeva
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  11. S. O. Bachurin
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Corresponding author

Correspondence to A. Yu. Aksinenko.

Additional information

Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2103–2107, November, 2018.

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Sokolov, V.B., Aksinenko, A.Y., Epishina, T.A. et al. Synthesis and biological activity of 5-vinyl- and 5-allyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles. Russ Chem Bull 67, 2103–2107 (2018). https://doi.org/10.1007/s11172-018-2335-9

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  • DOI: https://doi.org/10.1007/s11172-018-2335-9

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