Abstract
In the present study, a series of N-substituted sulfonamides have been synthesized. The reaction of benzene sulfonyl chloride (1) with O-anisidine (2) yielded N-(2-methoxyphenyl) benzenesulfonamide (3), which on bromination 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 hydride yielded thirteen different N-substituted sulfonamides. The compounds were characterized by IR, EIMS and 1H-NMR and screened against acetyl cholinesterase, butyryl cholinesterase and lipoxygenase enzymes. The results revealed that N-butyl-N-(4, 5-dibromo-2-methoxyphenyl)benzene sulfonamide (6d) and N-pentyl-N-(4,5-dibromo-2-methoxy phenyl)benzenesulfonamide (6e) exhibited good inhibitory potential against lipoxygenase.
Highlights
Sulfonamides containing group –SO2NH- is a present in many pharmacologically active compounds [1]
The mechanism through which sulfonamides perform its function is to inhibit the conversion of p-amino benzoic acid, creating hurdle in utilization of p-amino benzoic acid for bacteria in folic acid synthesis which leads to formation of purine and DNA [3]
Literature survey revealed that minor modification in the structure of compound can result in qualitative as well as quantitative changes in the activity, which prompted us to carry out the synthesis of various sulfonamide derivatives of o-anisidine and to study their structure
Summary
Sulfonamides containing group –SO2NH- is a present in many pharmacologically active compounds [1]. Many infectious diseases caused by Gram-negative and Gram-positive bacteria are cured by widely used sulfonamides [4] These compounds find their wide application as antitumor, anticancer and anti-viral agent because they have been reported to inhibit cancer cell growth and to cease tumor invasion [2]. Some derivatives of sulfonamides are extensively used for gastrointestinal and urinary tract infections because of their ease of administration and non-interaction with defense mechanism of host [5]. All these findings encouraged us to explore the synthesis of different N-substituted sulfonamides derived from o-anisidine with improved and different biological activity. It was filtered, washed with water and crystallized from aqueous methanol
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