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SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL SCREENING OF VARIOUS N-SUBSTITUTED DERIVATIVES OF SULFONAMIDES

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Author(s): AZIZ-UR-REHMAN, WAJEEHA TANVEER, MUHAMMAD ATHAR ABBASI, SUMBAL AFROZ, KHALID MOHAMMED KHAN, MUHAMMAD ASHRAF, AND IFTIKHAR AFZAL

Journal: International Journal of Chemical Research
ISSN 0975-3699

Volume: 3;
Issue: 3;
Start page: 99;
Date: 2011;
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Keywords: O-anisodine | Sulfonamide | butyryl cholinesterase | lipoxygenase and 1H-NMR

ABSTRACT
In the present study, a series of N-substituted sulfonamides have been synthesized. The reaction ofbenzene sulfonyl chloride (1) with O-anisidine (2) yielded N-(2-methoxyphenyl) benzenesulfonamide (3), which onbromination with bromine in the presence of acetic acid gave N-(4,5-dibromo-2-methoxyphenyl)benzenesulfonamide(6). The two products (3) and (6) further on treatment with alkyl halides/acyl halide in the presence of sodium hydrideyielded thirteen different N-substituted sulfonamides. The compounds were characterized by IR, EIMS and 1H-NMRand screened against acetyl cholinesterase, butyryl cholinesterase and lipoxygenase enzymes. The results revealedthat N-butyl-N-(4, 5-dibromo-2-methoxyphenyl)benzene sulfonamide (6d) and N-pentyl-N-(4,5-dibromo-2-methoxyphenyl)benzenesulfonamide (6e) exhibited good inhibitory potential against lipoxygenase.
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