- Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.
Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.
Bioorganic & medicinal chemistry letters (2014-04-02)
Vladimir Burmistrov, Christophe Morisseau, Kin Sing Stephen Lee, Diyala S Shihadih, Todd R Harris, Gennady M Butov, Bruce D Hammock
PMID24685540
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 (IC50=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).
MATERIALS