Synthesis, Characterization and Enzyme Inhibition Studies on Various O-Substituted Derivatives of N-(4-Hydroxyphenyl)-N-methyl-O-phenyl carbamate

Abstract

In the present study, a series of O-substituted carbamates have been synthesized. The reaction of 4-(aminomethyl) phenol (1) with phenylchloroformate (2) yielded N-(4-hydroxyphenyl)-N-methyl-O-phenyl carbamate (3). This product 3 on treatment with alkyl/aryl halides in the presence of lithium hydride yielded ten different O-substituted carbamates. All newly synthesized compounds were characterized by IR, EI-MS and ¹H-NMR  spectra and then screened against ????-chymotrypsin, acetylcholinesterase, and butyrylcholinesterase enzymes. The results revealed that N-(4-benzoxyphenyl)-N-methyl-O-phenyl carbamate (8b), N-[4-(2-chlorobenzoxy)phenyl]-N-methyl-O-phenyl carbamate (8c), and N-[4-(4-chlorobenzoxy)phenyl]-Nmethyl-O-phenyl carbamate (8e) exhibited good inhibitory potential against acetylcholinesterase and butyrylcholinesterase and are possible target molecule for the treatment of Alzheimer's disease.