Identification of benzofuran central cores for the inhibition of leukotriene A(4) hydrolase

Bioorg Med Chem Lett. 2013 Feb 1;23(3):811-5. doi: 10.1016/j.bmcl.2012.11.074. Epub 2012 Dec 5.

Abstract

Leukotrienes (LT's) are known to play a physiological role in inflammatory immune response. Leukotriene A(4) hydrolase (LTA(4)H) is a cystolic enzyme that stereospecifically catalyzes the transformation of LTA(4) to LTB(4). LTB(4) is a known pro-inflammatory mediator. This paper describes the identification and synthesis of substituted benzofurans as LTH(4)H inhibitors. The benzofuran series demonstrated reduced mouse and human whole blood LTB(4) levels in vitro and led to the identification one analog for advanced profiling. Benzofuran 28 showed dose responsive target engagement and provides a useful tool to explore a LTA(4)H inhibitor for the treatment of inflammatory diseases, such as asthma and inflammatory bowel disease (IBD).

MeSH terms

  • Animals
  • Benzofurans / chemistry*
  • Benzofurans / pharmacology
  • Dose-Response Relationship, Drug
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley

Substances

  • Benzofurans
  • Enzyme Inhibitors
  • Epoxide Hydrolases
  • benzofuran
  • leukotriene A4 hydrolase