Skip to main content

Reaction of 5-O-succinoylavermectin B1 with alkylating agents

Abstract

A reaction of 5-O-succinoylavermectin B1 with alkylating agents, namely phenacyl halides, bromoacetanilides, and benzyl bromides, was studied. Esters of 5-O-succinoylavermectin B1 were obtained for the first time, which are of interest as potential antiparasitic agents.

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

References

  1. 1.

    W. C. Campbell, R. W. Burg, M. H. Fisher, R. A. Dybas, The Discovery of Ivermectin and Other Avermectin, ACS Symposium Series No. 255, Am. Chem. Soc., Washington,1984, 5.

    Google Scholar 

  2. 2.

    A. Crump, S. Omura, Proc. Jpn Acad. Ser. B. Phys. Biol. Sci., 2011, 87, 13.

    CAS  Article  Google Scholar 

  3. 3.

    F. M. Marty, C. M. Lowry, M. Rodriguez, D. A. Milner, W. S. Pieciak, A. Sinha, L. Fleckenstein, L. R. Baden, Clin. Infect. Dis., 2005, 41(1), e5.

    Article  Google Scholar 

  4. 4.

    M. Kh. Dzhafarov, F. I. Vasilevich, Adv. Pharmacol. Pharmacy, 2014, 2, 30.

    Google Scholar 

  5. 5.

    W. C. Campbell, M. H. Fisher, E. O. Stapely, G. A. Schotberg, T. A. Jacob, Science, 1983, 26, 823.

    Article  Google Scholar 

  6. 6.

    M. Kh. Dzhafarov, I. V. Zavarzin, M. N. Mirzaev, Z. A. Devrishova, Yu. A. Yusupov, Sel’skokhozyaistvennaya biologiya. Seriya Biologiya zhivotnykh [Agricultural Biology. Series Animal Biology], 2012, 2, 96 (in Russian).

    Google Scholar 

  7. 7.

    M. N. Mirzaev, S. N. Savchenkov, T. P. Zharova, D. A. Devrishov, E. S. Voronin, in Problemy infektsionnykh i invazionnykh boleznei v zhivotnovodstve na sovremennom etape [Nowadays Problems of Infectious and Invasive Diseases in Cattle Breeding], Moscow, 1999, 272 (in Russian).

    Google Scholar 

  8. 8.

    F. Echevarría, M. Borba, A. Pinheiro, P. Waller, J. Hansen, Vet. Parasitol., 1996, 62, 199.

    Article  Google Scholar 

  9. 9.

    N. G. Guseinov, S. A. Mel’nitskii, M. N. Mirzaev, O. Kh. Manzhiev, Vet. meditsina [Vet. Medicine], 2007, 2–3, 34 (in Russian).

    Google Scholar 

  10. 10.

    I. Fairweather, J. S. Gilleard, Parasitology, 2007, 8, 40.

    Google Scholar 

  11. 11.

    K. Tyrell, F. Leo, Parasitology, 2009, 11, 98.

    Google Scholar 

  12. 12.

    M. Várady, J. orba, V. Letková, G. Ková, Vet. Parasitol., 2009, 2–3, 267.

    Article  Google Scholar 

  13. 13.

    M. S. Khalil, J. Plant Pathology Microbiology, 2013, 4(4), 32.

    Article  Google Scholar 

  14. 14.

    Y. Lin-Fang, W. Shan-Shan, W. Fu-Rong, C. Jun, T. NingNing, Ningxia Yixue Zazhi, 2012, 34(6), 491.

    Google Scholar 

  15. 15.

    J.-P. Lumaret, F. F. Errouissi, K. Rombke, J. Wardhaugh, Curr. Pharm. Biotechnol., 2012, 13(6), 1004.

    CAS  Article  Google Scholar 

  16. 16.

    G. H. Zhang, Y. G. Zhong-qiu, Zhonghua Weisheng Shachong Yaoxie, 2012, 18(6), 65.

    CAS  Google Scholar 

  17. 17.

    E. I. Chernoburova, K. V. Danchenko, M. A. Shchetinina, A. A. Zharov, A. V. Kolobov, M. Kh. Dzhafarov, F. I. Vasilevich, I. V. Zavarzin, Russ. Chem. Bull. (Int. Ed.), 2016, 2952 [Izv. Akad. Nauk, Ser. Khim., 2016, 2952].

    Google Scholar 

  18. 18.

    E. I. Chernoburova, E. S. Polyukhova, M. A. Shchetinina, A. V. Kolobov, M. Kh. Dzhafarov, F. I. Vasilevich, I. V. Zavarzin, Russ. Chem. Bull. (Int. Ed.), 2016, 2956 [Izv. Akad. Nauk, Ser. Khim., 2016, 2956].

    Google Scholar 

  19. 19.

    Pat. RF 2453553; Byul. izobret. [Invention Bull.], 2012, No. 17 (in Russian).

  20. 20.

    Pat. RF 2472801; Byul. izobret. [Invention Bull.], 2013, No. 2 (in Russian).

  21. 21.

    I. V. Zavarzin, E. S. Kuleshova, E. I. Chernoburova, M. A. Shchetinina, A. V. Kolobov, V. V. Plakhtinskii, M. Kh. Dzhafarov, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 538 [Izv. Akad. Nauk, Ser. Khim., 2014, 538].

    CAS  Article  Google Scholar 

  22. 22.

    M. Kh. Dzhafarov, M. N. Mirzaev, I. V. Zavarzin, Sel’skokhozyaistvennaya biologiya. Seriya Biologiya zhivotnykh [Agricultural Biology. Series Animal Biology], 2011, 2, 108 (in Russian).

    Google Scholar 

  23. 23.

    M. Kh. Dzhafarov, M. N. Mirzaev, I. V. Zavarzin, Z. A. Devrishova, M. N. Mirzaev, Zhurn. veterinarnoi meditsiny [J. Vet. Medicine], 2012, 1, 37 (in Russian).

    Google Scholar 

  24. 24.

    Z. A. Devrishova, M. N. Mirzaev, M. N. Dzhafarov, M. N. Karsakov, Yu. A. Yusupov, T. I. Mel’nitskaya, Zhurn. veterinarnoi meditsiny [J. Vet. Medicine], 2012, 2, 25 (in Russian).

    Google Scholar 

  25. 25.

    E. I. Olekhnovich, S. A. Roslavtseva, M. A. Alekseev, K. M. Mirzaeva, M. Kh. Dzhafarov, A. V. Kolobov, A. I. Sapozhnikova, I. V. Zavarzin, Yu. A. Yusupov, Zhurn. veterinarnoi meditsiny [J. Vet. Medicine], 2013, 4, 28 (in Russian).

    Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to I. V. Zavarzin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2965–2969, December, 2016.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Chernoburova, E.I., Lishchuk, V.A., Ovchinnikov, K.L. et al. Reaction of 5-O-succinoylavermectin B1 with alkylating agents. Russ Chem Bull 65, 2965–2969 (2016). https://doi.org/10.1007/s11172-016-1686-3

Download citation

Key words

  • avermectin B1
  • 5-O-succinoylavermectin B1
  • phenacylhalides
  • bromoacetanilides
  • benzyl bromides
  • esters of 5-O-succinoylavermectin B1
  • alkylation
  • antiparasitic activity