Novel inhibitors of fatty acid oxidation as potential metabolic modulators

Bioorg Med Chem Lett. 2004 Feb 23;14(4):973-7. doi: 10.1016/j.bmcl.2003.11.065.

Abstract

We describe the synthesis of novel inhibitors of fatty acid oxidation as potential metabolic modulators for the treatment of stable angina. Replacement of the 2H-benzo[d]1,3-dioxolene ring system in our initial lead 3 with different benzthiazoles, benzoxazoles and introducing small alkyl substituents into the piperazine ring resulted in analogues with enhanced inhibitory activity against 1-(14)[C]-palmitoyl-CoA oxidation in isolated rat heart mitochondria (6, IC(50)=70 nM; 25, IC(50)=23 nM).

MeSH terms

  • Animals
  • Epoxy Compounds / pharmacology*
  • Fatty Acids / metabolism*
  • Humans
  • Liver / drug effects
  • Liver / enzymology
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Mitochondria, Heart / drug effects
  • Mitochondria, Heart / metabolism
  • Molecular Structure
  • Oxidation-Reduction / drug effects
  • Palmitoyl Coenzyme A / drug effects
  • Palmitoyl Coenzyme A / metabolism
  • Rats
  • Structure-Activity Relationship

Substances

  • Epoxy Compounds
  • Fatty Acids
  • Palmitoyl Coenzyme A