Salicylate-urea-based soluble epoxide hydrolase inhibitors with high metabolic and chemical stabilities

Bioorg Med Chem Lett. 2009 Mar 15;19(6):1784-9. doi: 10.1016/j.bmcl.2009.01.069. Epub 2009 Jan 27.

Abstract

We investigated N-adamantyl-N'-phenyl urea derivatives as simple sEH inhibitors. Salicylate ester derivatives have high inhibitory activities against human sEH, while the free benzoic acids are less active. The methyl salicylate derivative is a potent sEH inhibitor, which also has high metabolic and chemical stabilities; suggesting that such inhibitors are potential lead molecule for bioactive compounds acting in vivo.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Benzoates / chemistry
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Epoxide Hydrolases / chemistry
  • Humans
  • Hydrogen Bonding
  • Hydrolysis
  • Hypertension / drug therapy
  • Inhibitory Concentration 50
  • Kinetics
  • Models, Chemical
  • Salicylates / chemistry*
  • Spectrometry, Fluorescence / methods
  • Urea / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Benzoates
  • Salicylates
  • Urea
  • Epoxide Hydrolases