Synthesis, Bacterial biofilm inhibition and cytotoxicity of new N-Alkyl/aralkyl-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-nitrobenzenesulfonamides

The current research was commenced by reaction of 1,4-benzodioxane-6-amine (1) with 4-nitrobenzenesulfonyl chloride (2) in the presence of aqueous base under dynamic pH control at 9 to yield N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-nitrobenzenesulfonamide (3) which was further reacted with a series of alkyl/aralkyl halides (4a-i) in polar aprotic solvent using catalytic amount of lithium hydride which acts as base to afford some new N-alkyl/aralkyl-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-nitrobenzenesulfonamides (5a-i). The projected structures of all the synthesized derivatives were characterized by contemporary techniques i.e., IR, 1H-NMR and EIMS. The biofilm Inhibitory action of all synthesized molecules was carried out against Escherichia coli and Bacillus subtilis. It was inferred from their results that 5f and 5e exhibited suitable inhibitory action against the biofilms of these bacterial strains. Moreover, their cytotoxicity was also checked and it was concluded that these synthesized molecules displayed docile cytotoxicity.