Synthesis and SAR of conformationally restricted inhibitors of soluble epoxide hydrolase

Paul D. Jones, Hsing Ju Tsai, Zung N. Do, Christophe Morisseau, Bruce D. Hammock

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

A series of conformationally restricted inhibitors of human soluble epoxide hydrolase (sEH) has been developed. Inhibition potency of the described compounds ranges from 4.2 μM to 1.1 nM against recombinant sEH. N-(1-Acetylpiperidin-4-yl)-N′-(adamant-1-yl) urea (5a) was found to be a potent inhibitor (IC50 = 7.0 nM) that was also orally bioavailable in canines.

Original languageEnglish (US)
Pages (from-to)5212-5216
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number19
DOIs
StatePublished - Oct 1 2006

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Epoxide Hydrolases
Inhibitory Concentration 50
Urea
Canidae

Keywords

  • Enzyme inhibition
  • Soluble epoxide hydrolase
  • Structure-activity relationships

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis and SAR of conformationally restricted inhibitors of soluble epoxide hydrolase. / Jones, Paul D.; Tsai, Hsing Ju; Do, Zung N.; Morisseau, Christophe; Hammock, Bruce D.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 16, No. 19, 01.10.2006, p. 5212-5216.

Research output: Contribution to journalArticle

Jones, Paul D. ; Tsai, Hsing Ju ; Do, Zung N. ; Morisseau, Christophe ; Hammock, Bruce D. / Synthesis and SAR of conformationally restricted inhibitors of soluble epoxide hydrolase. In: Bioorganic and Medicinal Chemistry Letters. 2006 ; Vol. 16, No. 19. pp. 5212-5216.
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