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Bioorg Med Chem Lett. 2014 May 1;24(9):2193-7. doi: 10.1016/j.bmcl.2014.03.016. Epub 2014 Mar 20.

Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.

Author information

  • 1Department of Chemistry and General Chemical Technology, Volzhsky Polytechnic Institute (branch) Volgograd State Technical University, Volzhsky, Russia; Volgograd State Technical University, Volgograd, Russia.
  • 2Department of Entomology and Nematology, Comprehensive Cancer Center, University of California at Davis, One Shields Avenue, Davis, CA 95616, USA.
  • 3Department of Entomology and Nematology, Comprehensive Cancer Center, University of California at Davis, One Shields Avenue, Davis, CA 95616, USA. Electronic address: bdhammock@ucdavis.edu.

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).

Copyright © 2014 Elsevier Ltd. All rights reserved.

KEYWORDS:

Adamantane; Diurea; Inhibitor; Isocyanate; Soluble epoxide hydrolase

PMID:
24685540
[PubMed - indexed for MEDLINE]
PMCID:
PMC4019751
Free PMC Article
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