Synthesis and inhibitory activity of 1,3-(adamantan-1(2)-yl)- imidazolidine-2,4,5-triones and 3,3'-(adamantan-1-yl)- bis(1-alkylimidazolidine-2,4,5-triones)

A series of 1,3-(adamantan-1(2)-yl)imidazolidine-2,4,5-triones and 1,1'-(alkane-1,n-diyl)bis[3-(adamantan-1-yl)imidazolidine-2,4,5-triones] was synthesized via cyclization of 1,3-bis[adamantan-1(2)-ylureas] and 1,1'-(alkyl-1,n-diyl)bis[3-(adamantan-1-yl)ureas] with oxalyl chloride under mild conditions with high yields. All synthesized compounds were tested in vitro as inhibitors of soluble human epoxide hydrolase. A number of compounds have high inhibitory activity (IC50 1.6–650 nM), which makes them promising inhibitors of soluble epoxide hydrolase.