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Russian Chemical Bulletin

, Volume 63, Issue 2, pp 538–542 | Cite as

Synthesis and biological activity of new avermectin 5-O- and 4″-O-acyl derivatives

  • I. V. ZavarzinEmail author
  • E. S. Kuleshova
  • E. I. Chernoburova
  • M. A. Shchetinina
  • A. V. Kolobov
  • V. V. Plakhtinskii
  • M. Kh. Dzhafarov
Full Articles

Abstract

Acylation of avermectin B1 with vicinal 1,2-dicarboxylic acid anhydrides leads only to 5-O-acyl derivatives in high yields. Avermectin 4″-O-acyl derivatives were obtained under similar conditions from avermectin B1 5-O-TBS-derivatives in good yields. The compounds obtained are of interest as antiparasitic agents.

Key words

avermectin B1 1,2-dicarboxylic acid anhydrides avermectin B1 5-O- and 4″-O-acylated derivatives antiparasitic and medicinal agents veterinary medicine 

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References

  1. 1.
    M. A. Alekseev, S. A. Roslavtseva, Agrokhimiya [Agrichemistry], 2006, 1, 71 (in Russian).Google Scholar
  2. 2.
    T. A. Blizzard, H. Mrozik, M. H. Fisher, Tetrahedron Lett., 1988, 29, 3163.CrossRefGoogle Scholar
  3. 3.
    B. Fraser-Reid, H. Wolleb, R. Faghih, J. Barchi, J. Am. Chem. Soc., 1987, 109, 933.CrossRefGoogle Scholar
  4. 4.
    M. H. Fisher, Pure Appl. Chem., 1990, 62, 1231.CrossRefGoogle Scholar
  5. 5.
    N. G. Guseinov, S. A. Mel’nitskii, M. N. Mirzaev, O. Kh. Mandzhiev, Veterinarnaya meditsina [Veterinary medicine], 2007, No. 2–3, 34 (in Russian).Google Scholar
  6. 6.
    K. Tyrell, F. Leo, Veterinary Parasitology, 2009, 11, 98.Google Scholar
  7. 7.
    M. Varady, J. Cobra, V. Letkova, G. Kovac, Veterinary Parasitology, 2009, 2–3, 267.CrossRefGoogle Scholar
  8. 8.
    H. Mrozik, P. Eskola, M. H. Fisher, J. R. Egerton, S. Cifelli, D. A. Ostlind, J. Med. Chem., 1982, 25, 658.CrossRefGoogle Scholar
  9. 9.
    K. Nagai, T. Sunazuka, S. Omura, Tetrahedron Lett., 2004, 45, 2507.CrossRefGoogle Scholar
  10. 10.
    K. Nagai, T. Sunazuka, K. Shiomi, A. Harder, A. Turberg, S. Omura, Bioorg. Med. Chem. Lett., 2003, 3943.Google Scholar
  11. 11.
    Pat. RF 2453553; Byul. izobret. [Invention Bull.], 2012, No. 17 (in Russian); Pat. RF 2472801; Byul. izobret. [Invention Bull.], 2013 (in Russian).Google Scholar
  12. 12.
    Pat. RF 2013053; Byul. izobret. [Invention Bull.], 1994 (in Russian).Google Scholar
  13. 13.
    Preparativnaya organicheskaya khimiya [Preparative Organic Chemistry], Eds N. S. Vul’fson and N. F. Tsvetkov, Goskhimizdat, Moscow, 1959, 688 pp. (in Russian).Google Scholar
  14. 14.
    A. J. Gordon, R. A. Ford, A Chemists Companion: A Handbook of Practical Data, Techniques, and References, Wiley Intersci., New York-London-Sydney-Toronto, 1972, 537 pp.Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • I. V. Zavarzin
    • 1
    Email author
  • E. S. Kuleshova
    • 2
  • E. I. Chernoburova
    • 1
  • M. A. Shchetinina
    • 1
  • A. V. Kolobov
    • 2
  • V. V. Plakhtinskii
    • 2
  • M. Kh. Dzhafarov
    • 3
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Yaroslavl State Technical UniversityYaroslavlRussian Federation
  3. 3.K. I. Skryabin Moscow State Academy of Veterinary Medicine and BiotechnologyMoscowRussian Federation

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