Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VI. N-[Fluoro(chloro)phenyl]-N′-(4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptan-1-yl)ureas

Abstract

The reaction of (S)-(–)-1-isocyanato-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one with fluoro- and chloro-substituted anilines afforded a series of N,N′-disubstituted ureas containing a natural lipophilic camphanic acid moiety in 42–75% yield. The synthesized compounds are promising as inhibitors of human soluble epoxide hydrolase.