Skip Navigation
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.


The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Your Environment. Your Health.

Publication Detail

Title: Bioisosteric substitution of adamantane with bicyclic lipophilic groups improves water solubility of human soluble epoxide hydrolase inhibitors.

Authors: Burmistrov, Vladimir; Morisseau, Christophe; Karlov, Dmitry; Pitushkin, Dmitry; Vernigora, Andrey; Rasskazova, Elena; Butov, Gennady M; Hammock, Bruce D

Published In Bioorg Med Chem Lett, (2020 09 15)

Abstract: A series of inhibitors of the soluble epoxide hydrolase (sEH) containing lipophilic groups of natural origin (camphanyl, norcamphanyl, furan-2-yl) were developed. Inhibitory potency ranging from 0.4 nM to 2.16 μM were obtained. While having the same level of inhibitory activity bicyclic ureas are up to 10-fold more soluble than the corresponding ureas containing adamantyl or 4-trifluoromethoxyphenyl substituents. This makes them easier to formulate, more bioavailable and thus more promising as therapeutic sEH inhibitors. Endo/exo-form of compound 2b derived from l-camphor is 14-fold more potent than the corresponding analogue derived from d-camphor (IC50 = 3.7 nM vs. 50.6 nM) indicating enantiomeric preference.

PubMed ID: 32736212 Exiting the NIEHS site

MeSH Terms: Adamantane/chemistry*; Adamantane/metabolism; Binding Sites; Enzyme Inhibitors/chemistry*; Enzyme Inhibitors/metabolism; Epoxide Hydrolases/antagonists & inhibitors*; Humans; Lipids/chemistry*; Molecular Docking Simulation; Protein Binding; Solubility; Stereoisomerism; Structure-Activity Relationship; Urea/analogs & derivatives; Urea/chemistry; Water

to Top