Synthesis and properties of 1-[(adamantan-1-yl)methyl]-3-pyrazolyl ureas

A series of 1,3-disubstituted ureas containing 1,3,5-trisubstituted pyrazole and (adamantan-1-yl)methyl fragments were synthesized in the reaction of 1-(isocyanatomethyl)adamantane with 3- or 4-aminopyrazoles under mild conditions in 67-92% yields. The inhibitory activity of the obtained compounds w...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-02, Vol.55 (2), p.129-134
Main Authors: D’yachenko, Vladimir S., Danilov, Dmitry V., Shkineva, Tatyana K., Vatsadze, Irina А., Burmistrov, Vladimir V., Butov, Gennady M.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Hydrolases
Organic Chemistry
Pharmacy
Protein kinases
Pyrazole
Technical institutes
Ureas
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Summary:A series of 1,3-disubstituted ureas containing 1,3,5-trisubstituted pyrazole and (adamantan-1-yl)methyl fragments were synthesized in the reaction of 1-(isocyanatomethyl)adamantane with 3- or 4-aminopyrazoles under mild conditions in 67-92% yields. The inhibitory activity of the obtained compounds with respect to human soluble epoxide hydrolase (sEH) was 16.2-50.2 nmol/l, with solubility in water of 45-85 μmol/l.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-019-02428-2