Advertisement

Russian Chemical Bulletin

, Volume 60, Issue 11, pp 2401–2405 | Cite as

1,3-Cycloaddition synthesis of 1,2,3-triazole conjugates of betulonic acid with peptides

  • A. I. Govdi
  • S. F. Vasilevsky
  • V. G. Nenajdenko
  • N. V. Sokolova
  • G. A. Tolstikov
Full Articles

Abstract

1,2,3-Triazole conjugates of betulonic acid with peptides were synthesized by 1,3-dipolar cycloaddition of azido peptides to N-(3-oxolup-20(29)-en-28-oyl)-4-ethynylaniline.

Key words

triterpenoids betulonic acid arylacetylenes azides peptides 1,3-dipolar cycloaddition 1,2,3-triazoles 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. S. Butler, Nat. Prod. Rep., 2008, 25, 475.CrossRefGoogle Scholar
  2. 2.
    V. M. Dembitskii, G. A. Tolstikov, Prirodnye galogenirovannye organicheskie soedineniya [Natural Galogenated Organic Compounds], Izd-vo SO RAN, Filial “Geo”, 2003, 363 pp. (in Rissian).Google Scholar
  3. 3.
    T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Bioorg. Khim., 2006, 32, 291 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 32].Google Scholar
  4. 4.
    G. A. Tolstikov, L. A. Baltina, V. P. Grankina, R. M. Kondratenko, T. G. Tolstikova, Solodka: bioraznoobrazie, khimiya, primenenie v meditsine [Licorice: Biodiversity, Chemistry, Application in Medicine], Izd-vo “Geo”, 2007, 308 pp. (in Russian).Google Scholar
  5. 5.
    S. F. Vasilevsky, A. I. Govdi, I. V. Sorokina, T. G. Tolstikova, G. A. Tolstikov, V. I. Mamatuyk, I. V. Alabugin, Bioorg. Med. Chem. Lett., 2011, 21, 62.CrossRefGoogle Scholar
  6. 6.
    Y. L. Angell, K. Burgess, Chem. Soc. Rev., 2007, 36, 1674.CrossRefGoogle Scholar
  7. 7.
    J. M. Holub, K. Kirshenbaum, Chem. Soc. Rev., 2010, 39, 1325.CrossRefGoogle Scholar
  8. 8.
    C. W. Tornøe, C. Cristensen, M. Meldal, J. Org. Chem., 2002, 67, 3057.CrossRefGoogle Scholar
  9. 9.
    V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 114, 2708.CrossRefGoogle Scholar
  10. 10.
    M. Meldal, C. W. Tornøe, Chem. Rev., 2008, 108, 2952.CrossRefGoogle Scholar
  11. 11.
    S. F. Vasilevsky, A. I. Govdi, E. E. Shul’ts, M. M. Shakirov, I. V. Alabugin, G. A. Tolstikov, Dokl. Akad. Nauk, 2009, 424, 631 [Dokl. Chem. (Engl. Transl.), 2009, 424, 39].Google Scholar
  12. 12.
    A. Domling, I. Ugi, Angew. Chem., Int. Ed., 2000, 39, 3168.CrossRefGoogle Scholar
  13. 13.
    A. Domling, Chem. Rev., 2006, 106, 17.CrossRefGoogle Scholar
  14. 14.
    A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, V. G. Nenajdenko, Chem. Rev., 2010, 110, 5235.CrossRefGoogle Scholar
  15. 15.
    A. G. Zhdanko, V. G. Nenajdenko, J. Org. Chem., 2009, 884.Google Scholar
  16. 16.
    A. G. Zhdanko, A. V. Gulevich, V. G. Nenajdenko, Tetrahedron, 2009, 4629.Google Scholar
  17. 17.
    A. V. Gulevich, N. E. Shevchenko, E. S. Balenkova, G.-V. Röschenthaler, V. G. Nenajdenko, Synlett, 2009, 403.Google Scholar
  18. 18.
    V. G. Nenajdenko, A. V. Gulevich, E. S. Balenkova, Tetrahedron, 2006, 5922.Google Scholar
  19. 19.
    V. G. Nenajdenko, A. V. Gulevich, E. S. Balenkova, J. Org. Chem., 2007, 7878.Google Scholar
  20. 20.
    A. V. Gulevich, N. E. Shevchenko, E. S. Balenkova, G.-V. Röschenthaler, V. G. Nenajdenko, Tetrahedron, 2008, 11706.Google Scholar
  21. 21.
    V. G. Nenajdenko, A. V. Gulevich, N. V. Sokolova, A. V. Mironov, E. S. Balenkova, Eur. J. Org. Chem., 2010, 1445.Google Scholar
  22. 22.
    T. A. Prikhod’ko, S. F. Vasilevsky, M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 2602 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1984, 33, 2383].Google Scholar
  23. 23.
    M. Kuroyanagi, M. Shiotsu, T. Ebihara, H. Kawai, A. Ueno, S. Fukushima, Chem. Pharm. Bull., 1986, 34, 4012.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • A. I. Govdi
    • 1
  • S. F. Vasilevsky
    • 1
  • V. G. Nenajdenko
    • 2
  • N. V. Sokolova
    • 2
  • G. A. Tolstikov
    • 3
  1. 1.Institute of Chemical Kinetics and CombustionSiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation
  2. 2.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation
  3. 3.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation

Personalised recommendations