Synthesis,structural characterization and biological screening of various sulfa drugs derived from 2-anisidine

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 npropyl- n-(2-methoxyphenyl)-4-methylbenzenesulfonamide (5c),n-(4,5-dibromo-2-methoxyphenyl)- 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.