N-{3-[2-(4-alkoxyphenoxy)thiazol-5-yl]-1-methylprop-2-ynyl}carboxy derivatives as acetyl-coA carboxylase inhibitors--improvement of cardiovascular and neurological liabilities via structural modifications

J Med Chem. 2007 Mar 8;50(5):1078-82. doi: 10.1021/jm070035a. Epub 2007 Feb 14.

Abstract

A preliminary safety evaluation of ACC2 inhibitor 1-(S) revealed serious neurological and cardiovascular liabilities of this chemotype. A systematic structure-toxicity relationship study identified the alkyne linker as the key motif responsible for these adverse effects. Toxicogenomic studies in rats showed that 1-(R) and 1-(S) induced gene expression patterns similar to that seen with several known cardiotoxic agents such as doxorubicin. Replacement of the alkyne with alternative linker groups led to a new series of ACC inhibitors with drastically improved cardiovascular and neurological profiles.

MeSH terms

  • Acetyl-CoA Carboxylase / antagonists & inhibitors*
  • Administration, Oral
  • Animals
  • Blood Pressure / drug effects*
  • Gene Expression / drug effects
  • Heart Rate / drug effects*
  • Infusions, Intravenous
  • Male
  • Myocardium / metabolism
  • Oligonucleotide Array Sequence Analysis
  • Rats
  • Rats, Sprague-Dawley
  • Seizures / chemically induced*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / adverse effects
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Thiazoles
  • Acetyl-CoA Carboxylase