Hair growth stimulator property of thienyl substituted pyrazole carboxamide derivatives as a CB1 receptor antagonist with in vivo antiobesity effect

Bioorg Med Chem Lett. 2009 May 1;19(9):2546-50. doi: 10.1016/j.bmcl.2009.03.046. Epub 2009 Mar 17.

Abstract

A few thienyl substituted pyrazole derivatives were synthesized to aid in the characterization of the cannabinoid receptor antagonist and also to serve as potentially useful antiobesity agent. Structural requirements for selective CB1 receptor antagonistic activity of 5-thienyl pyrazole derivatives included the structural similarity with potent, specific antagonist rimonabant 1. Compound 3 has been identified as a hair growth stimulator and an antiobesity agent in animal models.

MeSH terms

  • Animals
  • Benzoxazines / pharmacology
  • CHO Cells
  • Chemistry, Pharmaceutical / methods*
  • Cricetinae
  • Cricetulus
  • Cyclic AMP / metabolism
  • Drug Design
  • Hair / drug effects*
  • Inhibitory Concentration 50
  • Models, Chemical
  • Morpholines / pharmacology
  • Naphthalenes / pharmacology
  • Obesity / drug therapy*
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacology
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
  • Rimonabant

Substances

  • Benzoxazines
  • Morpholines
  • Naphthalenes
  • Piperidines
  • Pyrazoles
  • Receptor, Cannabinoid, CB1
  • Win 55212-2
  • Cyclic AMP
  • Rimonabant