Synthesis, Antibacterial and Lipoxygenase Inhibition Studies of N-(Alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides

Objectives: The present research work was aimed to synthesize some new sulfonamides bearing 1,4-benzodioxin ring, which might have suitable antibacterial potential and can be used as possible therapeutic agents for inflammatory ailments.

Materials and Methods: The synthesis was accomplished by the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) using 10% aqueous Na2CO3 to afford N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (3). Further the parent molecule 3 was reacted with different alkyl/aralkyl halides (4a-e) to achieve N-(alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides (5a-e), using polar aprotic solvent; N,N-dimethylformamide (DMF) and catalytic amount of lithium hydride as base. The characterization of synthesized compounds was conducted by contemporary spectral techniques e.g., IR, 1H-NMR and EI-MS. Then these molecules were subjected to screening against various bacterial strains and their inhibitory potential against Lipoxygenase was also ascertained.

Results: The screening results against various Gram-positive and Gram-negative bacterial strains revealed that N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (3), N-(2-bromoethyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5a) and N-(2-phenethyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5b) showed good inhibitory activity as compared to standard Ciprofloxacin. Moreover, N-(3-phenylpropyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5c) and N-(4-chlorobenzyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfon-amide (5e) displayed decent inhibition against lipoxygenase enzyme relative to standard Baicalein.

Conclusion: On the basis of results obtained it can be concluded that the synthesized sulfonamides may provide an overall indispensable basis to introduce new drug candidates for the cure of inflammatory and other associated diseases.