Skip to main content
SpringerLink
Log in

Synthesis and biological activity of amides of 28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oic acid

  • Published:
Chemistry of Natural Compounds Aims and scope

New A-seco-lupane C-3 amide conjugates were prepared by the reaction of 28-methoxy-28-oxo-1-cyano2,3-seco-lup-20(29)-en-3-oic acid chloride with primary amines and synthetic and natural amino acids. Ethyl-N-[28-methyl-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oyl]-β-alaninate, which was cytotoxic against rhabdomyosarcoma tumor cells (IC50 47.5 μM), in addition to ethyl-N-[28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oyl]glycinate and N-[28-methyl-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oyl]-2-aminothiazole, which inhibited reproduction of herpes simplex virus type 1 (EC50 35.1 and 30.9 1 M, respectively), were selected.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. W. J. Baas, Phytochemistry, 24(9), 1875 (1985).

    Article  CAS  Google Scholar 

  2. M. Urban, J. Sarek, J. Klinot, G. Korinkova, and M. Hajduch, J. Nat. Prod., 67, 1100 (2004).

    Article  PubMed  CAS  Google Scholar 

  3. O. B. Kazakova, E. F. Khusnutdinova, O. S. Kukovinets, T. I. Zvereva, and G. A. Tolstikov, Khim. Prir. Soedin., 333 (2010).

  4. I. A. Tolmacheva, V. V. Grishko, E. I. Boreko, O. V. Savinova, and N. I. Pavlova, Khim. Prir. Soedin., 566 (2009).

  5. Y. Wei, C.-M. Ma, and M. Hattori, Bioorg. Med. Chem., 17(8), 3003 (2009).

    Article  PubMed  CAS  Google Scholar 

  6. Y. Wei, C.-M. Ma, and M. Hattori, Eur. J. Med. Chem., 44(10), 4112 (2009).

    Article  PubMed  CAS  Google Scholar 

  7. M. Urban, J. Sarek, I. Tislerova, P. Dzubak, and M. Hajduch, Bioorg. Med. Chem., 13, 5527 (2005).

    Article  PubMed  CAS  Google Scholar 

  8. N. V. Galaiko, I. A. Tolmacheva, V. V. Grishko, L. V. Volkova, E. N. Perevozchikova, and S. A. Pestereva, Bioorg. Khim., 36(4), 556 (2010).

    PubMed  CAS  Google Scholar 

  9. I. A. Tolmacheva, E. V. Igosheva, V. V. Grishko, O. S. Zhukova, and G. K. Gerasimova, Bioorg. Khim., 36(3), 410 (2010).

    PubMed  CAS  Google Scholar 

  10. D. A. Scudiero, R. H. Shoemaker, K. D. Paull, A. Monks, S. Tierney, T. H. Notziger, M. T. Currens, D. Seniff, and M. K. Boyd, Cancer Res., 48, 4827 (1988).

    PubMed  CAS  Google Scholar 

  11. B. Keil, Laboratoriumstechnik der Organische Chemie, Akademie-Verlag, Berlin, 1961.

    Google Scholar 

  12. I. A. Tolmacheva, A. V. Nazarov, O. A. Maiorova, and V. V. Grishko, Khim. Prir. Soedin., 491 (2008).

  13. E. I. Boreko, N. I. Pavlova, G. V. Zaitseva, and I. A. Mikhailopulo, Vopr. Virusol., 5, 40 (2001).

    Google Scholar 

  14. K. P. Fung, Comput. Biol. Med., 19(2), 131 (1989).

    Article  PubMed  CAS  Google Scholar 

  15. P. G. Rytik, G. van der Groen, V. F. Eremin, N. D. Kolomiets, S. A. Popov, P. Nijs, V. Willems, G. Verkauteren, Yu. G. Il′kevich, and N. N. Lemeshko, Vopr. Virusol., 35(5), 389 (1990).

    PubMed  CAS  Google Scholar 

  16. I. I. Kucherov, P. G. Rytik, and I. A. Podol′skaya, in: Proceedings of the IInd Scientific-Practical Conf. on Progress of GNTP Infectious Diseases, 1998–2000, Minsk, 2001, p. 195.

  17. R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, and E. De Clereq, J. Virol. Methods, 20(4), 309 (1988).

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgment

The work was supported financially by State Contract No. 11.519.11.2033; RFBR Grant No. 10-03-96044; and the Ministry of Education, Perm Territory, for the performance of the MIG scientific project.

Author information

Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 614013, Russia, Perm

    E. V. Igosheva, I. A. Tolmacheva, Yu. B. Vikharev & V. V. Grishko

  2. Research Center for Epidemiology and Microbiology, Ministry of Health, Republic of Belarus, 220114, Belarus, Minsk

    O. V. Savinova, E. I. Boreko & V. F. Eremin

Authors
  1. E. V. Igosheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. A. Tolmacheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. B. Vikharev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Grishko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. V. Savinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. I. Boreko
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. F. Eremin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Grishko.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2012, pp. 385–389.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Igosheva, E.V., Tolmacheva, I.A., Vikharev, Y.B. et al. Synthesis and biological activity of amides of 28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oic acid. Chem Nat Compd 48, 426–431 (2012). https://doi.org/10.1007/s10600-012-0266-5

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-012-0266-5

Keywords

Search

Navigation