Medicinal Chemistry Research

, Volume 26, Issue 7, pp 1415–1426 | Cite as

Synthesis and analgesic activity of monoterpenoid-derived alkyl-substituted chiral hexahydro-2H-chromenes

  • Irina Il’ina
  • Alla Pavlova
  • Dina Korchagina
  • Oleg Ardashov
  • Tat’yana Tolstikova
  • Konstantin Volcho
  • Nariman Salakhutdinov
Original Research
First Online:
Received:
Accepted:

Abstract

A set of new 2-alkyl-substituted 4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols was obtained by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic aldehydes in the presence of montmorillonite clay K10. Synthesized compounds were evaluated for their analgesic activity in vivo using the acetic acid-induced writhing test and the hot-plate test. Five compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two of them also demonstrated analgesic activity in the hot-plate test. These compounds seem to be most promising for further development.

Keywords

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

Acknowledgements

Authors are grateful to the Russian Foundation for Basic Research (Grant No. 15-33-20198) for the financial support

Conflict of interest

The authors declare that they have no competing interests.

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Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  1. 1.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of SciencesNovosibirskRussian Federation
  2. 2.Novosibirsk State UniversityNovosibirskRussian Federation

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