Synthesis and Antimuscarinic Activity of 2-(N-(Ethyl)-(N-Beta-Hydroxyethyl))Aminoethyl 2,2-Diphenylpropionate, a Metabolite of Aprophen

摘要

The preparation of 2-(N-(ethyl)-(N-beta-hydroxyethyl)aminoethyl 2,2-diphenylpropionate (1) a metabolite of aprophen 12-diethylaminoethyl 2,2-diphenylpropionate) is described. Hydrolysis of 2-(2-chloroethyl)ethylaminolethyl acetate hydrochloride (2) in a basic solution, followed by acidic pH adjustment, gave the ethylcholineaziridinium ion (3) that upon treatment with 2,2-diphenylpropionic acid produced (1) in a 56% yield. Synthetic (1) was found to possess antimuscarinic activities, but was approx. 10-fold less potent than the parent compound aprophen.... Aprophen, Desethylaprophen, Atropine, The muscarinic receptors, Organophosphate antidote.