Synthesis of 2-[6-(2,4-dinitrophenoxy)hexyl]oxiranecarboxylic acid: a selective carnitine palmitoyltransferase-1 inhibitor

Bioorg Med Chem. 1998 Nov;6(11):2133-8. doi: 10.1016/s0968-0896(98)00175-8.

Abstract

Carnitine palmitoyltransferases 1 and 2 (CPT-1 and CPT-2) catalyze the transfer of long chain fatty acids between carnitine and coenzyme A. Unlike CPT-2, CPT-1 exists in at least two isoforms with different physical and kinetic properties. Liver and skeletal muscle each contain a different isoform of CPT-1. Cardiac muscle contains both isoforms, and the minor component is identical to the isoform found in the liver. 2-[6-(2,4-Dinitrophenoxy)hexyl]oxiranecarboxylic acid (2) was reported to be a selective inhibitor for the liver isoform of CPT-1. A synthesis of 2 is described here which involves the reaction of diethyl malonate with 1-bromo-6-phenoxyhexane.

MeSH terms

  • Animals
  • Carnitine O-Palmitoyltransferase / antagonists & inhibitors*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / pharmacology
  • Indicators and Reagents
  • Isoenzymes / antagonists & inhibitors*
  • Liver / enzymology
  • Molecular Conformation
  • Molecular Structure
  • Muscle, Skeletal / enzymology
  • Myocardium / enzymology

Substances

  • 2-(6-(2,4-dinitrophenoxy)hexyl)oxirane carboxylic acid
  • Enzyme Inhibitors
  • Epoxy Compounds
  • Indicators and Reagents
  • Isoenzymes
  • Carnitine O-Palmitoyltransferase