Chemistry of Natural Compounds

, Volume 54, Issue 2, pp 305–309 | Cite as

Addition of Cyanoethyl Groups to Ring a of Triterpenoids

  • N. V. Galaiko
  • I. A. Tolmacheva
  • E. V. Igosheva
  • O. V. Savinova
  • V. V. Grishko

The potential for cyanoethylation of ring A of triterpenoids and their A-seco derivatives prepared from allobetulone and methyl betulonate was investigated. Triterpenoids with a cyanoethyl moiety on C-1, C-2, and C-3 and derivatives with two cyanoethyl groups on ring A were synthesized. The inhibitory activity of the synthesized compounds for herpes simplex virus type 1 was studied in vitro.


triterpenoids A-seco-triterpenoids betulin cyanoethylation acrylonitrile antiviral activity herpes simplex virus type 1 



The work was financially supported by the Government of Perm Krai in the framework of Science Project No. C-26/056, grants MK-5386.2016.3, RFBR No. 16-53-00029Bel_a and BRFBR No. M16R-012.


  1. 1.
    F. F. Fleming and B. C. Shook, Tetrahedron, 58, 1 (2002).CrossRefGoogle Scholar
  2. 2.
    R. Garcia-Alvarez, J. Francos, E. Tomas-Mendivil, P. Crochet, and V. Cadierno, J. Organomet. Chem., 771, 93 (2014).CrossRefGoogle Scholar
  3. 3.
    R. Lopez and C. Palomo, Angew. Chem., Int. Ed. Engl., 54 (45), 13170 (2015).CrossRefGoogle Scholar
  4. 4.
    M. X. Wang, Acc. Chem. Res., 48 (3), 602 (2015).CrossRefPubMedGoogle Scholar
  5. 5.
    F. F. Fleming, Nat. Prod. Rep., 16, 597 (1999).CrossRefGoogle Scholar
  6. 6.
    F. F. Fleming, L. Yao, P. C. Ravikumar, L. Funk, and B. C. Shook, Med. Chem., 53, 7902 (2010).CrossRefGoogle Scholar
  7. 7.
    T. Honda, B. A. V. Rounds, G. W. Gribble, N. Suh, Y. Wang, and M. B. Sporn, Bioorg. Med. Chem. Lett., 8, 2711 (1998).CrossRefPubMedGoogle Scholar
  8. 8.
    M. Masullo, C. Pizza, and S. Piacente, Expert Opin. Ther. Pat., 27, 237 (2017).CrossRefPubMedGoogle Scholar
  9. 9.
    A. V. Shernyukov, N. F. Salakhutdinov, and G. A. Tolstikov, Russ. Chem. Bull., 62, 878 (2013).CrossRefGoogle Scholar
  10. 10.
    A. N. Antimonova, N. V. Uzenkova, N. I. Petrenko, M. M. Shakirov, E. E. Shul’ts, and G. A. Tolstikov, Russ. J. Org. Chem., 47 (4), 589 (2011).CrossRefGoogle Scholar
  11. 11.
    O. B. Kazakova, G. V. Giniyatullina, G. A. Tolstikov, I. P. Baikova, L. Zaprutko, and G. N. Apryshko, Russ. J. Bioorg. Chem., 37 (3), 369 (2011).CrossRefGoogle Scholar
  12. 12.
    G. V. Giniyatullina, O. B. Kazakova, N. I. Medvedeva, I. V. Sorokina, N. A. Zhukova, T. G. Tolstikova, and G. A. Tolstikov, Russ. J. Bioorg. Chem., 39 (3), 329 (2013).CrossRefGoogle Scholar
  13. 13.
    A. S. Kaledina, A. D. Zorina, V. V. Zarubaev, V. V. Anokhina, E. B. Erkhitueva, and R. E. Trifonov, Russ. J. Org. Chem., 51 (11), 1627 (2015).CrossRefGoogle Scholar
  14. 14.
    A. N. Volkova, “Synthesis of new N-containing lupane-type triterpenoids,” Candidate Dissertation, NIOCh, SB, RAS, Novosibirsk, 2014, 177 pp.Google Scholar
  15. 15.
    A. N. Antimonova, N. I. Petrenko, E. E. Shul’ts, and G. A. Tolstikov, in: Proceedings of the XIIIth Youth School-Conference “Critical Problems in Organic Chemistry” [in Russian], Novosibirsk, 2010, p.85.Google Scholar
  16. 16.
    F. N. Lugemwa, F.-Y. Huang, M. D. Bentley, M. J. Mendel, and A. R. Alford, J. Agric. Food Chem., 38, (2), 493 (1990).CrossRefGoogle Scholar
  17. 17.
    R. Pettit, N. Melody, F. Hempenstall, J.-C. Chapuis, T. L. Groy, and L. Williams, J. Nat. Prod., 77, 863 (2014).CrossRefPubMedPubMedCentralGoogle Scholar
  18. 18.
    I. A. Tolmacheva, A. V. Nazarov, O. A. Maiorova, and V. V. Grishko, Chem. Nat. Compd., 44, 606 (2008).CrossRefGoogle Scholar
  19. 19.
    F. F. Fleming and Q. Wang, Chem. Rev., 103, 2035 (2003).CrossRefPubMedGoogle Scholar
  20. 20.
    O. B. Kazakova, G. V. Giniyatullina, and G. A. Tolstikov, Russ. J. Bioorg. Chem., 37 (5), 619 (2011).CrossRefGoogle Scholar
  21. 21.
    V. V. Grishko, N. V. Galaiko, I. A. Tolmacheva, I. I. Kucherov, V. F. Eremin, E. I. Boreko, O. V. Savinova, and P. A. Slepukhin, Eur. J. Med. Chem., 83, 601 (2014).CrossRefPubMedGoogle Scholar
  22. 22.
    L. V. Anikina, I. A. Tolmacheva, Yu. B. Vikharev, and V. V. Grishko, Russ. J. Bioorg. Chem., 36, 240 (2010).CrossRefGoogle Scholar
  23. 23.
    A. V. Korovin and A. V. Tkachev, Russ. Chem. Bull., Int. Ed., 50, 304 (2001).CrossRefGoogle Scholar
  24. 24.
    R. Csuk, A. Niesen-Barthel, R. Schafer, A. Barthel, and A. Al-Harrasi, Eur. J. Med. Chem., 92, 700 (2015).CrossRefPubMedGoogle Scholar
  25. 25.
    K. P. Fung, Comput. Biol. Med., 19, 131 (1989).CrossRefPubMedGoogle Scholar

Copyright information

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

Authors and Affiliations

  • N. V. Galaiko
    • 1
  • I. A. Tolmacheva
    • 1
  • E. V. Igosheva
    • 1
  • O. V. Savinova
    • 2
  • V. V. Grishko
    • 1
  1. 1.Institute of Technical Chemistry, Ural BranchRussian Academy of SciencesPermRussia
  2. 2.The Republican Research and Practical Center for Epidemiology and MicrobiologyMinistry of Health of the Republic of BelarusMinskBelarus

Personalised recommendations