Bioisosteric replacement of the pyrazole 5-aryl moiety of N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A). A novel series of alkynylthiophenes as potent and selective cannabinoid-1 receptor antagonists

J Med Chem. 2008 Sep 11;51(17):5397-412. doi: 10.1021/jm800066v. Epub 2008 Aug 20.

Abstract

Replacing the conventional pyrazole 5-aryl substituent of 1 (SR141716A) with the 2-thienyl moiety appended with an appropriate alkynyl unit, a novel class of 5-(5-alkynyl-2-thienyl)pyrazole derivatives, behaving as highly potent CB1 receptor antagonists with good CB1/2 selectivity, was discovered, many of which, as typified by compound 18, showed significant weight reduction in diet-induced obese mouse model, thus pharmacologically validating that the bioisosteric replacement described above is viable. Also encouraging was the finding that a subtle structural modification of the newly developed series could result in a distinct difference in the intrinsic property, as demonstrated by compounds 12 (NA) and its methylated structural isomers 15 (PA) and 18 (IA). Moreover, current structure-activity relationship studies revealed that around the pyrazole 5-position of 1, a deep and flat crevice surrounded by a sequence of hydrophobic/aromatic residues as indicated by the CB1-receptor homology model might exist in the binding site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Hydrophobic and Hydrophilic Interactions
  • Mice
  • Mice, Obese
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
  • Rimonabant
  • Structure-Activity Relationship
  • Thiophenes / chemistry
  • Thiophenes / pharmacology*
  • Weight Loss / drug effects*

Substances

  • Piperidines
  • Pyrazoles
  • Receptor, Cannabinoid, CB1
  • Thiophenes
  • pyrazole
  • Rimonabant