Synthesis and Biological Activity of (Z)-Dialkylaminoalkylamides of N-Benzoyl-α,β-Dehydroamino Acids and Their Iodomethylates

Abstract

A series of N,N-(dialkylamino)alkylamides of several N-substituted α,β-dehydroamino acids and their quaternary ammonium salts were synthesized via the reaction of unsaturated 5(4H)-oxazolones with N,N-dialkyldiamines and characterized by physicochemical characteristics. Their reactions with human erythrocytic acetylcholinesterase (ACE) and plasmic butyrylcholinesterase (BuCE) were studied. The IC₅₀ values [concentration at which the hydrolysis rate of cholinesterase was 50% inhibited by acetylthiocholine (0.1 mM)] of all synthesized compounds were determined. It was found that all synthesized compounds possessed anticholinesterase activity and were specific mainly for BuCE.