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

Asian Journal of Pharmaceutical and Health Sciences,2012,2,4,461-466.
Published:November 2012
Type:Research Articles
Authors:
Author(s) affiliations:

Muhammad Athar Abbasi1*, Abdul Hafeez1, Aziz-ur-Rehman1, Khalid Mohammed Khan2, Muhammad Ashraf3, Syeda Abida Ejaz4

1Department of Chemistry, Government College University, Lahore-54000, Pakistan.

2HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan

3Department of Biochemistry and Biotechnology;

4Department of Pharmacy; The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan.

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)-Nmethyl-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 1 compounds were characterized by IR, EI-MS and H-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-Ophenyl 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.

Evaluation of enzyme inhibitory potential of the carbamates 6a-c and 8a-g. (n = 3, mean±sem)