Synthesis, structural characterization and biological screening of various sulfa drugs derived from 2-anisidine. | [Journal of Chemical Society of Pakistan • 2013]

Author(s):

1. Muhammad Athar Abbasi: Department of Chemistry, Government College University, Lahore, Pakistan

2. Aziz-Ur-Rehman: Department of Chemistry, Government College University, Lahore, Pakistan

3. Tahir Muhmood: Department of Chemistry, Government College University, Lahore, Pakistan

4. Khalid Mohammed Khan: HEJ Research Institute of Chemistry, International Centre for Chemical and Biological Sciences (ICCBS), University of Karachi, Karachi, Pakistan

5. Muhammad Ashraf: Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

6. Syeda Abida Ejaz: Department of Pharmacy, Islamia University of Bahawalpur, Bahawalpur, Pakistan

7. Samreen Arshad: Department of Pharmacy, Islamia University of Bahawalpur, Bahawalpur, Pakistan

Abstract:

In the present study, a series of N-alkyl substituted sulfa drugs (sulfonamides) has been synthesized. The reaction of 2-anisidine (1) with 4-methylbenzenesulfonyl chloride (2) yielded N-(2-methoxyphenyl)-4-methylbenzenesulfonamide (3), which on bromination with bromine in the presence of glacial acetic acid gave N-(4,5-dibromo-2-methoxyphenyl)-4-methylbenzenesulfonamide (6). These two products 3 and 6 on further treatment with different alkyl halides in the presence of lithium hydride yielded fourteen new N-substituted sulfonamides. These compounds were characterized by their EI-MS and 1H-NMR spectra and screened against acetylcholinesterase, butyrlcholinesterase and chymotrypsin enzymes. The results revealed that N-propyl-N-(2-methoxyphenyl)-4-methylbenzenesulfonamide (5c), N-(4,5-dibromo-2-methoxy-phenyl)-4-methylbenzenesulfonamide (6) and N-methyl-N-(4,5-dibromo-2-methoxyphenyl)-4-methylbenzenesulfonamide (7e) exhibited good inhibitory potential against acetylcholinesterase, butyrlcholinesterase and chymotrypsin respectively.

Page(s): 405-411

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 35, Issue: 2, Year: 2013

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