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Medicinal Chemistry Research

, Volume 24, Issue 11, pp 3821–3830 | Cite as

Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

  • Alla Pavlova
  • Oksana Mikhalchenko
  • Artem Rogachev
  • Irina Il’ina
  • Dina Korchagina
  • Yuriy Gatilov
  • Tat’yana Tolstikova
  • Konstantin VolchoEmail author
  • Nariman Salakhutdinov
Original Research

Abstract

2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (−)-α-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.

Keywords

Terpene Chromene Heterocyclic compounds Analgesic activity Acetic acid-induced writhing test Hot plate test Stereoisomers 

Notes

Acknowledgments

Authors are grateful to the Russian Foundation for Basic Research (Grant No 13-03-00206a) for the financial support.

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Alla Pavlova
    • 1
  • Oksana Mikhalchenko
    • 1
  • Artem Rogachev
    • 1
    • 2
  • Irina Il’ina
    • 1
    • 2
  • Dina Korchagina
    • 1
  • Yuriy Gatilov
    • 1
    • 2
  • Tat’yana Tolstikova
    • 1
  • Konstantin Volcho
    • 1
    • 2
    Email author
  • Nariman Salakhutdinov
    • 1
    • 2
  1. 1.Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussian Federation
  2. 2.Novosibirsk State UniversityNovosibirskRussian Federation

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