Identification and synthesis of novel inhibitors of acetyl-CoA carboxylase with in vitro and in vivo efficacy on fat oxidation

J Med Chem. 2010 Dec 23;53(24):8679-87. doi: 10.1021/jm101179e. Epub 2010 Nov 17.

Abstract

Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 ( Gargazanli , G. ; Lardenois , P. ; Frost , J. ; George , P. Patent WO9855474 A1, 1998 ) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m ( Zoller , G. ; Schmoll , D. ; Mueller , M. ; Haschke , G. ; Focken , I. Patent WO2010003624 A2, 2010 ) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / pharmacokinetics
  • Acetamides / pharmacology
  • Acetyl-CoA Carboxylase / antagonists & inhibitors*
  • Animals
  • Female
  • Hepatocytes / drug effects*
  • Hepatocytes / metabolism
  • Humans
  • Isoenzymes / antagonists & inhibitors
  • Mice
  • Mice, Obese
  • Oxidation-Reduction
  • Palmitic Acid / metabolism
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology
  • Rats
  • Rats, Wistar
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triglycerides / blood

Substances

  • Acetamides
  • Isoenzymes
  • N-(3-(4-(6-isopropoxypyridin-3-yloxy)phenyl)-1-methylpropyl)acetamide
  • Pyridines
  • Triglycerides
  • Palmitic Acid
  • Acetyl-CoA Carboxylase