Synthesis and Properties of N,N′-Disubstituted Ureas Containing Adamantane and Pyridine (Quinoline) Fragments

A series of N,N′-disubstituted ureas containing a pyridine or quinoline fragment and a lipophilic adamantane moiety (13 examples, 53–94% yield) have been synthesized by the reaction of N,N-dimethyl-N′-(pyridin-2-yl or quinoline-2-yl)ureas with amine hydrochlorides. The synthesized compounds differed from each other by the position of substitution in the adamantane fragment, structure of the alkyl linker between the adamantane fragment and amide group, and heterocyclic substituent. They are potential target-oriented inhibitors of human soluble epoxide hydrolase (sEH).