Structure-activity relationships of 3,5-disubstituted benzamides as glucokinase activators with potent in vivo efficacy

Bioorg Med Chem. 2009 Jun 1;17(11):3800-9. doi: 10.1016/j.bmc.2009.04.040. Epub 2009 Apr 24.

Abstract

The optimization of our lead GK activator 2a to 3-[(1S)-2-hydroxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]-N-1,3-thiazol-2-ylbenzamide (6g), a potent GK activator with good oral availability, is described, including to uncouple the relationship between potency and hydrophobicity. Following oral administration, this compound exhibited robust glucose lowering in diabetic model rodents.

MeSH terms

  • Animals
  • Benzamides / chemistry*
  • Benzamides / pharmacology*
  • Dogs
  • Enzyme Activation / drug effects*
  • Enzyme Activators / chemistry*
  • Enzyme Activators / pharmacology*
  • Glucokinase / chemistry*
  • Glucokinase / metabolism*
  • Humans
  • Male
  • Mice
  • Molecular Structure
  • Rats
  • Structure-Activity Relationship

Substances

  • Benzamides
  • Enzyme Activators
  • Glucokinase