Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors

Vladimir Burmistrov, Christophe Morisseau, Kin Sing Stephen Lee, Diyala S. Shihadih, Todd R. Harris, Gennady M. Butov, Bruce D. Hammock

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

A series of inhibitors of the soluble epoxide hydrolase (sEH) containing two urea groups has been developed. Inhibition potency of the described compounds ranges from 2.0 μM to 0.4 nM. 1,6-(Hexamethylene)bis[(adamant-1-yl) urea] (3b) was found to be a potent slow tight binding inhibitor (IC 50 = 0.5 nM) with a strong binding to sEH (Ki = 3.1 nM) and a moderately long residence time on the enzyme (koff = 1.05 × 10-3 s-1; t1/2 = 11 min).

Original languageEnglish (US)
Pages (from-to)2193-2197
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number9
DOIs
StatePublished - May 1 2014

Keywords

  • Adamantane
  • Diurea
  • Inhibitor
  • Isocyanate
  • Soluble epoxide hydrolase

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Medicine(all)

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