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Sulfonamides are considered to be pharmaceutically important class of compounds. In the present work, N-(2,4-dimethylphenyl)-4-toluenesulfonamide (3) was synthesized by the reaction of 2,4-dimethylaniline (1) and 4-tosyl chloride (2; 4-methylbenzenesulfonyl chloride) using 10% aqueous Na2CO3 solution as reaction medium. At the second step, the synthesized molecule 3 was made to react with different alkyl/aralkyl halides (4a-o) to yield the target compounds, 5a-o, using N,N-dimethylformamide (DMF) as reaction medium and lithium hydride as an activator. The synthesis of all the compounds was verified by spectral techniques using IR, 1H-NMR and EIMS; and further examined for their anti-enzymatic activities. The synthesized compound 5f represented a suitable inhibitory potential against α-glucosidase and lipoxygenase enzymes.