Ureas derived from camphor and fenchone reveal enantiomeric preference of human soluble epoxide hydrolase

1-(3-Chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea

“…Previously, we have observed synthesis and inhibitory activity against human soluble epoxide hydrolase (sEH) of multiple series of adamantyl-containing 1,3-disubstituted ureas and thioureas, and the same findings have been reported by our colleagues [1][2][3]. sEH is involved in the metabolism of epoxy fatty acids to corresponding vicinal diols through a catalytic addition of water [4,5].…”

“…We chose to use imine derived from camphor as a fragment for our new class of soluble epoxide hydrolase inhibitors for a number of reasons. First of all, substitution of adamantane with natural monoterpene fragments [2] or their simultaneous introduction into the same molecule [12] can provide great benefits in the field of green chemistry. Secondly, compounds containing imines derived from camphor possess various biological activities, including strong antiviral activity [13].…”

Solubility- and melting-based approaches to evaluate the inner-crystal enantiophobia and enantiophilia undergoing a structural change within a homologous series, exemplified by chiral glycerol ethers

“…1,3,13,14 They are also interested in other rare ways of crystallising chiral matter. [15][16][17][18][19][20][21][22][23][24][25][26][27][28] However, it is possible that the reasons for chiral discrimination lie precisely in trivial heterochiral crystallisation, which is much more common than homochiral crystallisation, and understanding these reasons may lead to insights into the relationship sought. In particular, it is possible to systematically change the structure of a chemical compound, analysing how this affects the manner it crystallises.…”