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Medicinal Chemistry Research

, Volume 22, Issue 6, pp 3026–3034 | Cite as

Synthesis and analgesic activity of new heterocyclic compounds derived from monoterpenoids

  • Oksana Mikhalchenko
  • Irina Il’ina
  • Alla Pavlova
  • Ekaterina Morozova
  • Dina Korchagina
  • Tat’yana Tolstikova
  • Evgeny Pokushalov
  • Konstantin VolchoEmail author
  • Nariman Salakhutdinov
Original Research

Abstract

A set of new heterocyclic compounds with different types of framework, including a new type of framework, were synthesized by reactions of verbenol epoxide and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes containing three methoxy groups. The analgesic activity of these substances was studied. Three compounds possessed considerable activity in vivo in the acetic acid-induced writhing test. (2S,4R,4aR,8S,8aR)-4,7-Dimethyl-2-(2,4,5-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-4,8-epoxychromene exhibited high analgesic activity in both acetic acid-induced writhing and hot plate tests; its selectivity index IS50 exceeded 60.

Keywords

Verbenol epoxide Terpenoid Heterocyclic compounds Analgesic activity Acetic acid-induced writhing test Hot plate test 

Notes

Acknowledgments

Authors are grateful to the Presidium of Russian Academy of Sciences (Program No. 28) and Russian Foundation for Basic Research (Grant No. 10-03-00230a) for the financial support.

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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • Oksana Mikhalchenko
    • 1
  • Irina Il’ina
    • 2
  • Alla Pavlova
    • 2
  • Ekaterina Morozova
    • 2
  • Dina Korchagina
    • 2
  • Tat’yana Tolstikova
    • 2
  • Evgeny Pokushalov
    • 3
  • Konstantin Volcho
    • 2
    Email author
  • Nariman Salakhutdinov
    • 2
  1. 1.Novosibirsk State UniversityNovosibirskRussian Federation
  2. 2.Novosibirsk Institute of Organic ChemistrySiberian Branch, Russian Academy of SciencesNovosibirskRussian Federation
  3. 3.State Research Institute of Circulation PathologyNovosibirskRussian Federation

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