Adamantyl-ureas with pyrazoles substituted by fluoroalkanes as soluble epoxide hydrolase inhibitors

Adamantyl-ureas with pyrazoles substituted by fluoroalkanes as soluble epoxide hydrolase inhibitors Full article

Journal

Journal of Fluorine Chemistry
ISSN: 1873-3328 , E-ISSN: 0022-1139

Output data

Year: 2023, Volume: 266, Article number : 110087, Pages count : DOI: 10.1016/j.jfluchem.2023.110087

Authors

Burmistrov Vladimir V. ^1,2 , Morisseau Christophe ² , Shkineva Tatyana K. ³ , Danilov Dmitry V. ¹ , Gladkikh Boris ¹ , Butov Gennady M. ¹ , Fayzullin Robert R. ⁴ , Dutova Tatyana Ya. ³ , Hammock Bruce D. ² , Dalinger Igor L. ³

Affiliations

1	Department of Chemistry, Technology and Equipment of Chemical Industry, Volzhsky Polytechnic Institute (branch) Volgograd State Technical University, 42a Engels Street, Volzhsky 404121, Russia
2	Department of Entomology and Nematology, and Comprehensive Cancer Center, University of California, Davis, CA 95616, USA
3	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Lenin Avenue, Moscow 119991, Russia
4	Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, Kazan 420088, Russia

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 (3f, IC50 = 0.8 nM) and 1-[(Adamantan-1-yl)methyl]-3-[(4,5-dichloro-1-methyl-1Н-pyrazol-3-yl)methyl]urea (4f, IC50 = 1.2 nM) were found to be the most potent sEH inhibitors within the described series.

Burmistrov V.V. , Morisseau C. , Shkineva T.K. , Danilov D.V. , Gladkikh B. , Butov G.M. , Fayzullin R.R. , Dutova T.Y. , Hammock B.D. , Dalinger I.L.
Adamantyl-ureas with pyrazoles substituted by fluoroalkanes as soluble epoxide hydrolase inhibitors
Journal of Fluorine Chemistry. 2023. V.266. 110087 . DOI: 10.1016/j.jfluchem.2023.110087 WOS Scopus OpenAlex

≡ Web of science:	WOS:000923687500001
≡ Scopus:	2-s2.0-85150775612
≡ OpenAlex:	W4318937373