Skip to main content
Log in

Structures and biological activity of cinnamoyl derivatives of coumarins and dehydroacetic acid and their boron difluoride complexes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Computer-assisted screening for Kohonen self-organizing maps in terms of the quantitative structure—activity relationship (QSAR) model revealed the high potential activity of cinnamoyl derivatives of coumarin and dehydroacetic acid and their boron difluoride complexes against a number of biological targets, including HIV-1 integrase. The pronounced inhibitory properties of dehydroacetic acid derivatives and their boron difluoride complexes against HIV-1 integrase were experimentally confirmed by in vitro testing of their antiviral activity with respect to HIV-infected cells. The data obtained suggests a correlation between the structure of the compounds studied and their biological activity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. P. Gupta, M. S. Babu, N. Kaw, J. Enzyme Inhib., 1999, 14, 109.

    Article  CAS  Google Scholar 

  2. G. Patonay, J. Salon, J. Sowell, L. Strekowski, Molecules, 2004, 9, 40.

    Article  CAS  Google Scholar 

  3. K. D. Volkova, V. B. Kovalska, A. I. Tatarets, I. D. Patsenker, D. V. Krivorotenko, S. M. Yarmoluk, Dyes Pigm., 2007, 72, 285.

    Article  CAS  Google Scholar 

  4. T. K. Chiu, D. R. Davies, Curr. Top. Med. Chem., 2004, 4, 965.

    Article  CAS  Google Scholar 

  5. Yu. Yu. Agapkina, T. A. Prikazchikova, M. A. Smolov, M. B. Gottikh, Usp. Biol. Khim. [Advances in Biological Chemistry], 2005, 45, 87 (in Russian).

    Google Scholar 

  6. Y. Pommier, N. Neamati, Adv. Virus Res., 1999, 52, 427.

    Article  CAS  Google Scholar 

  7. Y. Pommier, C. Marchand, N. Neamati, Antiviral Res., 2000, 47, 139.

    Article  CAS  Google Scholar 

  8. R. Dayam, N. Neamati, Curr. Pharm. Des., 2003, 9, 1789.

    Article  CAS  Google Scholar 

  9. R. Dayam, T. Sanchez, N. Neamati, J. Med. Chem., 2005, 48, 8009.

    Article  CAS  Google Scholar 

  10. J. Deng, T. Sanchez, I. Q. Al-Mawsawi, R. Dayam, R. A. Yunes, A. Garofalo, M. B. Bolger, N. Neamati, Bioorg. Med. Chem., 2007, 15, 4985.

    Article  CAS  Google Scholar 

  11. D. J. Hazuda, P. Felock, M. Witmer, A. Wolfe, K. Stillmock, J. A. Grobler, A. Espeseth, L. Gabryelski, W. Schleif, C. Blau, M. D. Miller, Science, 2000, 287, 646.

    Article  CAS  Google Scholar 

  12. D. J. Hazuda, N. J. Anthony, R. P. Gomez, S. M. Jolly, J. S. Wai, L. Zhuang, T. E. Fisher, M. Embrey, J. P. Guare, Jr., M. S. Egbertson, J. P. Vacca, J. R. Huff, P. J. Felock, M. V. Witmer, K. A. Stillmock, R. Danovich, J. Grobler, M. D. Miller, A. S. Espeseth, L. Jin, I.-W. Chen, J. H. Lin, K. Kassahun, J. D. Ellis, B. K. Wong, W. Xu, P. G. Pearson, W. A. Schleif, R. Cortese, E. Emini, V. Summa, M. K. Holloway, S. D. Young, Proc. Natl. Acad. Sci. USA, 2004, 101, 11233.

    Article  CAS  Google Scholar 

  13. V. F. Traven, A. V. Manaev, T. A. Chibisova, Dyes Pigm., 2003, 58, 41.

    Article  CAS  Google Scholar 

  14. A. V. Manaev, K. V. Tambov, V. F. Traven, Zh. Org. Khim., 2008, 44, 1064 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44].

    Google Scholar 

  15. V. F. Traven, A. V. Manaev, I. V. Voevodina, I. N. Okhrimenko, Izv. Akad. Nauk, Ser. Khim., 2008, 1479 [Russ. Chem. Bull., Int. Ed., 2008, 57, 1508].

    Google Scholar 

  16. A. V. Manaev, I. N. Okhrimenko, V. F. Traven, Izv. Akad. Nauk, Ser. Khim., 2008, 1701 [Russ. Chem. Bull., Int. Ed., 2008, 57].

  17. Ya. A. Ivanenkov, E. V. Bovina, K. V. Balakin, Usp. Khim., 2009, 78, 503 [Russ. Chem. Rev. (Engl. Transl.), 2009, 78].

    Article  Google Scholar 

  18. W. P. Walters, M. T. Stahl, M. A. Murcko, Drug Discovery Today, 1998, 3, 160.

    Article  CAS  Google Scholar 

  19. J. Bajorat, Nat. Rev. Drug Discovery, 2002, 1, 882.

    Article  Google Scholar 

  20. K. V. Balakin, Ya. A. Ivanenkov, A. V. Skorenko, S. N. Kovalenko, I. A. Zhuravel, V. P. Chernykh, Ukr. Zh. Org. Farm. Khim. [Ukranian Journal of Organic and Pharmaceutical Chemistry], 2004, 2, 47 (in Russian).

    CAS  Google Scholar 

  21. Y. Nikolsky, K. V. Balakin, Y. A. Ivanenkov, A. A. Ivashchenko, N. P. Savchuk, PharmaChem, 2003, 4, 68.

    Google Scholar 

  22. N. P. Savchuk, S. E. Tkachenko, K. V. Balakin, Methods and Principles in Medicinal Chemistry, Vol. 23, Chemoinformatics in Drug Discovery, Ed. T. I. Oprea, Wiley-VCH, Weinheim, 2005, 287.

    Google Scholar 

  23. K. V. Balakin, D. Sc. (Chem.) Thesis, Ivanovo State Univ., Ivanovo, 2005 (in Russian).

  24. Y. Nikolsky, K. V. Balakin, Y. A. Ivanenkov, A. A. Ivashchenko, N. Ph. Savchuk, J. Pharm. Chem., 2003, 4, 68.

    Google Scholar 

  25. Y. A. Ivanenkov, K. V. Balakin, A. V. Skorenko, S. E. Tkochenko, N. Ph. Savchuk, A. A. Ivashchenko, Y. Nikolsky, Chem. Today, 2003, 21, 72.

    CAS  Google Scholar 

  26. S. V. Trepalin, V. A. Gerasimenko, A. V. Kozyukov, N. Ph. Savchuk, A. A. Ivashchenko, J. Chem. Inf. Model., 2002, 42, 249.

    Article  CAS  Google Scholar 

  27. Y. A. Ivanenkov, L. M. Khandarova, in Pharmaceutical Data Mining: Approaches and Applications for Drug Discovery, Ed. K. V. Balakin, John Wiley and Sons, Inc., New York, 2009, 457.

    Google Scholar 

  28. K. V. Balakin, Y. A. Ivanenkov, N. P. Savchuk, in Chemogenomics: Methods and Applications, Ed. E. Jacoby, Humana Press-Springer, New York, 2009, p. 21.

    Google Scholar 

  29. Y. A. Ivanenkov, E. V. Bovina, K. V. Balakin, Usp. Khim., 2009, 78 [Russ. Chem. Rev. (Engl. Transl.), 2009, 78, 503].

    Google Scholar 

  30. I. Pletnev, Y. Ivanenkov, A. Tarasov, in Pharmaceutical Data Mining: Approaches and Applications for Drug Discovery, Ed. K. V. Balakin, John Wiley and Sons, Inc., New York, 2009, 425.

    Google Scholar 

  31. L. Guttmann, Psychometrika, 1954, 19, 149.

    Article  Google Scholar 

  32. R. B. Catell, S. A. Vogelmann, Multi Behav. Res., 1977, 12, 289.

    Article  Google Scholar 

  33. C. S. Peirce, A Theory of Probable Inference, Studies in Logic, Little, Brown, and Co., Boston, 1883, 126.

    Google Scholar 

  34. A. Pendri, N. A. Meanwell, K. M. Peese, M. A. Walker, Expert Opin. Ther. Pat., 2011, 21, 1173.

    Article  CAS  Google Scholar 

  35. K. Ramkumar, K. V. Tambov, R. Gundla, A. V. Manaev, V. Yarovenko, V. F. Traven, N. Neamati, Bioorg. Med. Chem., 2008, 16, 8988.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. F. Traven.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 76–88, January, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tambov, K.V., Voevodina, I.V., Manaev, A.V. et al. Structures and biological activity of cinnamoyl derivatives of coumarins and dehydroacetic acid and their boron difluoride complexes. Russ Chem Bull 61, 78–90 (2012). https://doi.org/10.1007/s11172-012-0012-y

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-012-0012-y

Key words

Navigation