Synthesis and biological evaluation of a novel 3-sulfonyl-8-azabicyclo[3.2.1]octane class of long chain fatty acid elongase 6 (ELOVL6) inhibitors

J Med Chem. 2009 Jul 23;52(14):4111-4. doi: 10.1021/jm900488k.

Abstract

Long chain fatty acid elongase 6 (ELOVL6) catalyzes the elongation of long chain fatty acyl-CoAs and is a potential target for the treatment of metabolic disorders. The ultrahigh throughput screen of our corporate chemical collections resulted in the identification of a novel 3-sulfonyl-8-azabicyclo[3.2.1]octane class of ELOVL6 inhibitor 1a. Optimization of lead 1a led to the identification of the potent, selective, and orally available ELOVL6 inhibitor 1w.

MeSH terms

  • Acetyltransferases / antagonists & inhibitors*
  • Animals
  • Cell Line
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Fatty Acid Elongases
  • Hepatocytes / drug effects
  • Hepatocytes / enzymology
  • Humans
  • Inhibitory Concentration 50
  • Liver / drug effects
  • Liver / enzymology
  • Male
  • Mice
  • Octanes / chemical synthesis*
  • Octanes / chemistry
  • Octanes / pharmacokinetics
  • Octanes / pharmacology*
  • Rats
  • Structure-Activity Relationship
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry*
  • Sulfones / pharmacokinetics
  • Sulfones / pharmacology*
  • Tropanes / chemical synthesis*
  • Tropanes / chemistry*
  • Tropanes / pharmacokinetics
  • Tropanes / pharmacology*

Substances

  • ELOVL6 protein, human
  • Elovl6 protein, mouse
  • Enzyme Inhibitors
  • Octanes
  • Sulfones
  • Tropanes
  • Acetyltransferases
  • Fatty Acid Elongases