Medicinal Chemical Studies on Synthetic Protease Inhibitors, trans-4-Guanidinomethylcyclohexanecarboxylic Acid Aryl Esters

trans-4-Guanidinomethylcyclohexanecarboxylic acid (trans-GMCHA) aryl esters were synthesized and tested for inhibitory effects on serine proteases, trypsin, chymotrypsin, plasmin, plasma kallikrein, pancreatic kallikrein, urokinase and thrombin. In general, these compounds showed strong inhibitory effects on chymotrypsin, pancreatic kallikrein and urokinase, but the effects varied greatly depending on the substituent in the benzene nucleus. Some of the trans-GMCHA aryl esters strongly inhibited compound 48/80-induced histamine release from mast cells / the p-tert-butylphenyl ester was especially active.