Substituted benzyl 7V-phenylcarbamates - Their solvolysis and inhibition activity to acetylcholinesterase and butyrylcholinesterase

Abstract

Kinetic evidence has indicated that methanolysis of synthesized 4-acetoxybenzyl carbamates proceeds via a one-step (concerted) mechanism. Concerted 1,6-elimination produces the very reactive 1,4-quinonemethide, which was trapped in the form of 4-methoxymethylphenol. The inhibition activity of benzyl N-phenylcarbamates to acetylcholinesterase (ACHE) and butyrylcholinesterase (BCHE) was also tested. The found IC50values varied within the limits of 199-535 μmo1 1-1 1for ACHE and 21-177 μmol lndash1for BCHE. The found values of partition coefficient (Pow) in the range of 1.5-11.5 represent a prerequisite of good transport of benzyl N-phenylcarbamates through haemato-encephalic barrier. © ARKAT USA, Inc.