Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes

Irina Il’ina, Ekaterina Morozova, Alla Pavlova, Dina Korchagina, Tat’yana Tolstikova, Konstantin Volcho, Nariman Salakhutdinov

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

New hexahydro-2H-chromenes were synthesized by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic ketones in the presence of montmorillonite clay H+-K10. The compounds formed and isolated as a pair of diastereoisomers were evaluated for their analgesic activity in vivo. It was found that the analgesic activity of (4aR,8R,8aR)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydrospiro[chromene-2,1ʹ-cyclohexane]-4,8-diol 8b significantly exceeds (two orders of magnitude higher) the activity of diclofenac sodium in the acetic acid-induced writhing test. It has low acute toxicity and is very promising for further development.

Original languageEnglish
Pages (from-to)738-747
Number of pages10
JournalMedicinal Chemistry Research
Volume29
Issue number4
DOIs
Publication statusPublished - 1 Apr 2020

Keywords

  • Acetic acid-induced writhing test
  • Analgesic activity
  • Chromene
  • Heterocyclic compounds
  • Hot plate test
  • Terpene
  • METHOXY GROUPS
  • HYDROXY
  • NATURAL-PRODUCTS

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