Skip to main content

Synthesis and antimicrobial and toxic properties of novel 1,3-bis(alkyl)-6-methyluracil derivatives containing 1,2,3- and 1,2,4-triazolium fragments

Russian Journal of Bioorganic Chemistry volume 43, pages 170–176 (2017)Cite this article

Abstract

The antimicrobial activity and cytotoxicity of novel 1,3-bis(alkyl)-6-methyluracil derivatives containing 1,2,3- and 1,2,4-triazolium fragments in alkyl chains have been studied. The compounds have been tested for the antimicrobial activity toward some gram-positive and gram-negative bacteria and fungal cultures. The cytotoxic action has been estimated toward mammalian cells. It has been found that the basic structural factor that affects the antimicrobial activity is the nature of alkyl radicals at triazole fragments.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

Abbreviations

MIC:

minimal inhibitory concentration

MBC:

minimal bactericidal concentration

MFC:

minimal fungicidal concentration

References

  1. Semenov, V.E., Voloshina, A.D., Kulik, N.V., Strobykina, A.S., Giniyatullin, R.Kh., Saifina, L.F., Nikolaev, A.E., Krylova, E.S., Zobov, V.V., and Reznik, V.S., Izv. Akad. Nauk, Ser. Khim., 2015, no. 12, pp. 2885–2896.

    Google Scholar 

  2. Semenov, V.E., Voloshina, A.D., Toroptzova, E.M., Kulik, N.V., Zobov, V.V., Giniyatullin, R.Kh., Mikhailov, A.S., Nikolaev, A.E., Akamsin, V.D., and Reznik, V.S., Eur. J. Med. Chem., 2006, vol. 41, pp. 1093–1101.

    CAS  Article  PubMed  Google Scholar 

  3. Semenov, V.E., Voloshina, A.D., Kulik, N.V., Uraleva, S.Yu., Giniyatullin, R.Kh., Mikhailov, A.S., Akamsin, V.D., Efremov, Yu.Ya, and Reznik, V.S., Khim.-Farm. Zh., 2009, vol. 43, pp. 21–26.

    Google Scholar 

  4. Nikolaev, A.E., Semenov, V.E., Voloshina, A.D., Kulik, N.V., and Reznik, V.S., Khim.-Farm. Zh., 2010, vol. 44, pp. 21–24.

    Google Scholar 

  5. Semenov, V.E., Mikhailov, A.S., Voloshina, A.D., Kulik, N.V., Nikitashina, A.D., Zobov, V.V., Kharlamov, S.V., Latypov, S.K., and Reznik, V.S., Eur. J. Med. Chem., 2011, vol. 46, pp. 4715–4724.

    CAS  Article  PubMed  Google Scholar 

  6. Gazieva, G.A. and Kravchenko, A.N., Usp. Khim., 2012, vol. 81, no. 6, pp. 494–523.

    CAS  Article  Google Scholar 

  7. Heeres, J., Hendrickx, R., and Van Cutsem, J., J. Med. Chem., 1983, vol. 26, no. 4, pp. 611–613.

    CAS  Article  PubMed  Google Scholar 

  8. Brodie, A., Trends Endocrin. Met., 2002, vol. 13, no. 2, pp. 61–65.

    CAS  Article  Google Scholar 

  9. Gabdrakhmanov, D.R., Samarkina, D.A., Semenov, V.E., Krylova, E.S., Reznik, V.S., and Zakharova, L.Ya., J. Mol. Liq., 2016, vol. 218, pp. 255–259.

    CAS  Article  Google Scholar 

  10. Semenov, V.E., Nikolaev, A.E., Krylova, E.S., Sharafutdinova, D.R., and Reznik, V.S., Zh. Org. Khim., 2012, vol. 48, pp. 582–587.

    CAS  Google Scholar 

  11. Ilker, F.M., Nusslein, K., Tew, G.N., and Coughlin, E.B., J. Am. Chem. Soc., 2004, vol. 126, pp. 15870–15875.

    CAS  Article  PubMed  Google Scholar 

  12. National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility. Tests for Bacteria That Grow Aerobically, 6th ed., Approved Standard, M7-A5, NCCLS, Wayne, USA, 2000.

  13. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi, Proposed Standard, M38-P, NCCLS, Wayne, USA, 1998.

  14. Kumar, R. and Banerjee, A.K., Cell. Mol. Life Sci., 1979, vol. 35, p. 160.

    CAS  Article  Google Scholar 

  15. Rajvaidya, N. and Markandey, D.K., Microbiology, Nangia, S.B., Ed., New Delhi: APH Publ. Corp., 2006.

Download references

Author information

Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, Kazan, 420088, Russia

    A. D. Voloshina, V. E. Semenov, A. S. Strobykina, N. V. Kulik, E. S. Krylova, V. V. Zobov & V. S. Reznik

Authors
  1. A. D. Voloshina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. E. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. S. Strobykina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Kulik
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. S. Krylova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. V. Zobov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. S. Reznik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. D. Voloshina.

Additional information

Proceedings of the Conference Chemical Biology-2016, (Novosibirsk, 24–29 July 2016).

Original Russian Text © A.D. Voloshina, V.E. Semenov, A.S. Strobykina, N.V. Kulik, E.S. Krylova, V.V. Zobov, V.S. Reznik, 2017, published in Bioorganicheskaya Khimiya, 2017, Vol. 43, No. 2, pp. 197–204.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Voloshina, A.D., Semenov, V.E., Strobykina, A.S. et al. Synthesis and antimicrobial and toxic properties of novel 1,3-bis(alkyl)-6-methyluracil derivatives containing 1,2,3- and 1,2,4-triazolium fragments. Russ J Bioorg Chem 43, 170–176 (2017). https://doi.org/10.1134/S1068162017020170

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162017020170

Keywords

  • triazoles
  • uracils
  • antimicrobial activity
  • cytotoxicity
  • hemolytic activity