Discovery of 3,3-disubstituted piperidine-derived trisubstituted ureas as highly potent soluble epoxide hydrolase inhibitors

Bioorg Med Chem Lett. 2009 Sep 15;19(18):5314-20. doi: 10.1016/j.bmcl.2009.07.138. Epub 2009 Aug 6.

Abstract

3,3-Disubstituted piperidine-derived trisubstituted urea entA-2b was discovered as a highly potent and selective soluble epoxide hydrolase (sEH) inhibitor. Despite the good compound oral exposure, excellent sEH inhibition in whole blood, and remarkable selectivity, compound entA-2b failed to lower blood pressure acutely in spontaneously hypertensive rats (SHRs). This observation further challenges the premise that sEH inhibition can provide a viable approach to the treatment of hypertensive patients.

MeSH terms

  • 8,11,14-Eicosatrienoic Acid / analogs & derivatives
  • 8,11,14-Eicosatrienoic Acid / blood
  • 8,11,14-Eicosatrienoic Acid / metabolism
  • Animals
  • Blood Pressure / drug effects
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Epoxide Hydrolases / metabolism*
  • Humans
  • Hypertension / drug therapy*
  • Models, Molecular
  • Piperidines / chemistry*
  • Protein Binding
  • Rats
  • Rats, Inbred SHR
  • Structure-Activity Relationship
  • Urea / analogs & derivatives*
  • Urea / pharmacology*
  • Urea / therapeutic use

Substances

  • 14,15-dihydroxyeicosatrienoic acid
  • Piperidines
  • piperidine
  • Urea
  • Epoxide Hydrolases
  • 8,11,14-Eicosatrienoic Acid