Several new and know sulfonamide Schiff bases were prepared by the condensation reaction of sulfonamide (i.e. 2-amino-4-chlorobenzenesulfonamide, sulfamerazine, sulfanilamide, sulfamethazine, sulfathiazole and sulfadiazine) with vanillin and salicylaldehyde, respectively in an acidic medium. These Schiff bases were used to a new series of β-lactam (azetidin-2-one) compounds (i.e. 4-chloro-2-(2-(4-hydroxy-3-methoxyphenyl)-3-mercapto-4-oxoazetidin-1-yl)benzenesulfonamide , 4-[2-aryl-3-mercapto (or 3-hydroseleno)-4-oxoazetidin-1-yl]-N-substituted benzenesulfonamide; Z5A1-Z5A6, Z5A9-Z5A12, Z5A2', Z5A9'-Z5A11') by their reactions with thioglycolic acid and 2-seleno-glycolic acid, respectively, in presences of phosphorus oxychloride and triethylamine. Cyclocondensation of the Schiff bases with 2-mercaptobutanoic acid in presence of zinc chloride afforded 4-thiazolidinone derivatives (i.e. 4-[5-ethyl-2-aryl-4-oxothiazolidin-3-yl]-N-substituted benzenesulfonamide; ZZ5A2-ZZ5A6, ZZ5A9-ZZ5A12). All new azetidin-2-one and 1,3-thiazolidin-4-one derivatives were characterized by IR, 1H NMR, 13C NMR, mass spectroscopic techniques and elemental analysis. The toxicity of new compounds was assayed via the determination of their LD50 value by using Dixon's up and down method. The antibacterial activity of azetidin-2-one compounds were tested in vitro against Staphylococcus aureus, Bacillus, Escherichia coli and Pseudomonas aeruginosa. Furthermore, the antioxidant and anticancer efficiency of compounds were evaluated.