Serendipity in drug-discovery: a new series of 2-(benzyloxy)benzamides as TRPM8 antagonists

Bioorg Med Chem Lett. 2013 Nov 15;23(22):6118-22. doi: 10.1016/j.bmcl.2013.09.016. Epub 2013 Sep 19.

Abstract

A new series of 2-(benzyloxy)benzamides are presented that are potent functional antagonists of TRPM8 and possess improved LipE and LE compared to the original lead. They were discovered through a series of compound libraries and we present a powerful visualization method for the chemical space explored with each library. Remarkably this new series originated from the highest risk design strategy where compounds were synthesised with the least degree of similarity to the lead structure.

Keywords: 1,3-Diamino cyclohexane; Lead hopping; Library design; Multi-dimensional scaling; TRPM8.

MeSH terms

  • Animals
  • Benzamides / pharmacology*
  • Drug Design
  • Drug Discovery
  • Humans
  • Rats
  • Structure-Activity Relationship
  • TRPM Cation Channels / antagonists & inhibitors*

Substances

  • Benzamides
  • TRPM Cation Channels
  • TRPM8 protein, human
  • Trpm8 protein, rat