Synthesis and analgesic activity of 1,3,5-trisubstituted pyrazoles containing a diterpenoid moiety

M. E. Mironov, A. I. Poltanovich, T. V. Rybalova, M. P. Dolgikh, T. G. Tolstikova, E. E. Shults

Research output: Contribution to journalArticlepeer-review

Abstract

Conjugates of terpenoids with 1,3,5-trisubstituted pyrazoles were synthesized by the cross-coupling of methyl 16-(2-chloro-2-oxoacetyl)labdatrienoate with terminal arylacetylenes via the Castro—Stephens reaction and heterocyclization of arylalkyne-1,2-diones with arylhydr-azines. The structure of one reaction product was established by X-ray diffraction. The conditions for the formation of furanolabdanoid arylalkyne-1,2-diones were found. The newly synthesized pyrazoles exhibit analgesic activity in a model of chemical irritation.

Original languageEnglish
Pages (from-to)537-546
Number of pages10
JournalRussian Chemical Bulletin
Volume69
Issue number3
DOIs
Publication statusPublished - Mar 2020

Keywords

  • alkyne-1,2-diones
  • Castro—Stephens cross-coupling
  • diterpenoids
  • furanolabdanoids
  • heterocyclization
  • phenyl-hydrazines
  • phlomisoic acid
  • pyrazoles
  • X-ray diffraction
  • SERIES
  • YNEDIONES
  • CRYSTAL-STRUCTURES
  • ALPHA
  • FURANODITERPENOIDS
  • alkyne-1
  • ACETYLENIC KETONES
  • LAMBERTIANIC ACID
  • DERIVATIVES
  • 2-diones
  • TRANSFORMATIONS
  • Castro-Stephens cross-coupling

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