Sulfonamides are considered to be pharmaceutically important class of compounds. In the present work, N-(2,4-dimethylphenyl)-4-toluenesulfonamide was synthesized by the reaction of 2,4-dimethylaniline and 4-tosyl chloride (4-methylbenzenesulfonyl chloride) using 10% aqueous Na2CO3 solution as reaction medium. At the second step, the synthesized molecule was made to react with different alkyl/aralkyl halides to yield the target compounds,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 compounds represented the most potential against α-glucosidase and lipoxygenase enzymes.