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Russian Chemical Bulletin

, Volume 63, Issue 5, pp 1130–1136 | Cite as

Synthesis and antiviral activity of bis-spirocyclic derivatives of rhodanine

  • S. V. Kurbatov
  • V. V. Zarubaev
  • L. A. Karpinskaya
  • A. A. Shvets
  • M. E. Kletsky
  • O. N. Burov
  • P. G. MorozovEmail author
  • O. I. Kiselev
  • V. I. Minkin
Full Articles

Abstract

Bis-spiro heterocycles containing spiro units at the 1,3-positions of the pyrrolizidine (isothiapyrrolizidine) moiety were synthesized by the reaction of unstabilized azomethine ylides, which were generated in situ from isatin and proline (isothiaproline), with hetarylidene-substituted rhodanines. Quantum chemical calculations of potential energy surface sections and descriptors controlling the regioselectivity of cycloaddition were carried out. For a number of compounds in vitro activity against the influenza virus A/California/07/09 (H1N1)pdm2009 was experimentally established.

Key words

spiro cycle rhodanine azomethine ylide 1,3-dipolar cycloaddition influenza antiviral drugs chemotherapy AM1 DFT B3LYP/6-31G** 

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • S. V. Kurbatov
    • 1
  • V. V. Zarubaev
    • 2
  • L. A. Karpinskaya
    • 2
  • A. A. Shvets
    • 1
  • M. E. Kletsky
    • 1
  • O. N. Burov
    • 1
  • P. G. Morozov
    • 1
    Email author
  • O. I. Kiselev
    • 2
  • V. I. Minkin
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussian Federation
  2. 2.Research Institute of InfluenzaSt. PetersburgRussian Federation

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