Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XVII. N-(3-Bromoadamantan-1-yl)-3-R-ureas and Symmetrical Bis-ureas

A series of N , N ′-disubstituted ureas and bis-ureas were synthesized in 36–85% yields by the reaction 3-bromoadamantan-1-yl isocyanate with α,ω-alkanediamines, fluorinated anilines, and trans -4-[(4-aminocyclo­hexyl)oxy]benzoic acid. The hydrolysis of 3-bromoadamant-1-yl isocyanate in the presence...

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Published inRussian journal of organic chemistry Vol. 59; no. 12; pp. 2138 - 2146
Main Authors Gladkikh, B. P., D’yachenko, V. S., Danilov, D. V., Matiukhina, A. K., Burmistrov, V. V., Butov, G. M.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.12.2023
Springer Nature
Springer Nature B.V
Subjects
Alkanes
Aniline
Benzoic acid
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Isocyanates
Organic Chemistry
Physical Sciences
Science & Technology
Ureas
bromine
adamantane
human soluble epoxide hydrolase (hsEH)
bromoadamantane
isocyanate
TARGET
SOLUBLE EPOXIDE HYDROLASE
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Summary:A series of N , N ′-disubstituted ureas and bis-ureas were synthesized in 36–85% yields by the reaction 3-bromoadamantan-1-yl isocyanate with α,ω-alkanediamines, fluorinated anilines, and trans -4-[(4-aminocyclo­hexyl)oxy]benzoic acid. The hydrolysis of 3-bromoadamant-1-yl isocyanate in the presence of a catalytic amount of DBU gave 60% of symmetrical N , N ′-bis(3-bromoadamantan-1-yl)urea. The synthesized compounds are promising as inhibitors of human soluble epoxide hydrolase (hsEH).
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023120114