Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

Bioorg Med Chem Lett. 2008 Jul 15;18(14):3882-6. doi: 10.1016/j.bmcl.2008.06.045. Epub 2008 Jun 18.

Abstract

Facile synthesis of biaryl pyrazole sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716, 1) and an investigation of the effect of replacement of the -CO group in the compound 1 by the -SO(2) group in the aminopiperidine region is reported. Primary ex-vivo pharmacological testing and in vitro screening of sulfonamide derivative 2 showed the loss of CB1 receptor antagonism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Inhibitory Concentration 50
  • Mice
  • Models, Chemical
  • Molecular Conformation
  • Piperidines / chemistry
  • Piperidines / pharmacology*
  • Pyrazoles / pharmacology*
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
  • Rimonabant
  • Sulfonamides / chemistry*

Substances

  • Piperidines
  • Pyrazoles
  • Receptor, Cannabinoid, CB1
  • Sulfonamides
  • Rimonabant