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Adamantyl-ureas with Pyrazoles Substituted by Fluoroalkanes As Soluble Epoxide Hydrolase Inhibitors

Overview
Journal J Fluor Chem
Specialty Chemistry
Date 2023 Aug 28
PMID 37638129
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Abstract

A series of soluble epoxide hydrolase (sEH) inhibitors containing halogenated pyrazoles was developed. Inhibition potency of the obtained compounds ranges from 0.8 to 27.5 nM. 1-Adamantyl-3-[(4,5-dichloro-1-methyl-1Н-pyrazol-3-yl)methyl]urea (, IC = 0.8 nM) and 1-[(Adamantan-1-yl)methyl]-3-[(4,5-dichloro-1-methyl-1Н-pyrazol-3-yl)methyl]urea (, IC = 1.2 nM) were found to be the most potent sEH inhibitors within the described series.

References
1.
Gillis E, Eastman K, Hill M, Donnelly D, Meanwell N . Applications of Fluorine in Medicinal Chemistry. J Med Chem. 2015; 58(21):8315-59. DOI: 10.1021/acs.jmedchem.5b00258. View

2.
Spector A, Fang X, Snyder G, Weintraub N . Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Prog Lipid Res. 2003; 43(1):55-90. DOI: 10.1016/s0163-7827(03)00049-3. View

3.
Spyra S, Meisner A, Schaefer M, Hill K . COX-2-selective inhibitors celecoxib and deracoxib modulate transient receptor potential vanilloid 3 channels. Br J Pharmacol. 2017; 174(16):2696-2705. PMC: 5522988. DOI: 10.1111/bph.13893. View

4.
Jeschke P . Latest generation of halogen-containing pesticides. Pest Manag Sci. 2017; 73(6):1053-1066. DOI: 10.1002/ps.4540. View

5.
Burmistrov V, Morisseau C, Dyachenko V, Rybakov V, Butov G, Hammock B . Fluoroaromatic fragments on 1,3-disubstituted ureas enhance soluble epoxide hydrolase inhibition. J Fluor Chem. 2020; 220:48-53. PMC: 7055688. DOI: 10.1016/j.jfluchem.2019.02.005. View