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Chemistry of Natural Compounds

, Volume 52, Issue 5, pp 813–820 | Cite as

Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2H-Chromen-4,8-Diols Containing Thiophene Substituents

  • A. V. Pavlova
  • E. V. Nazimova
  • O. S. Mikhal’chenko
  • I. V. Il’inaEmail author
  • D. V. Korchagina
  • O. V. Ardashov
  • E. A. Morozova
  • T. G. Tolstikova
  • K. P. Volcho
  • N. F. Salakhutdinov
Article

Hexahydro-2H-chromenes with thiophene fragments were synthesized via reactions of a p-menthane monoterpenoid diol with several thiophenecarboxaldehydes. Most of the synthesized compounds with an additional thiophene fragment displayed analgesic activity in vivo tests at a dose of 10 mg/kg. It was found that the activity in either an acetate-writhing test or a hot-plate test depended on the type and location of substituent in the heteroaromatic ring.

Keywords

monoterpenes thiophenecarboxaldehyde clay heterocyclic compounds analgesic activity 

Notes

Acknowledgment

We thank the Russian Foundation for Basic Research for financial support (Grant 15-33-20198) and the Khimiya Center for Collective Use, SB, RAS, for spectral and analytical measurements.

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • A. V. Pavlova
    • 1
  • E. V. Nazimova
    • 1
  • O. S. Mikhal’chenko
    • 1
  • I. V. Il’ina
    • 1
    • 2
    Email author
  • D. V. Korchagina
    • 1
  • O. V. Ardashov
    • 1
    • 2
  • E. A. Morozova
    • 1
  • T. G. Tolstikova
    • 1
  • K. P. Volcho
    • 1
    • 2
  • N. F. Salakhutdinov
    • 1
    • 2
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussian Federation
  2. 2.Novosibirsk National Research State UniversityNovosibirskRussian Federation

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