Synthesis, characterization and biological Activity of β-Lactam and Thiazolidinone Derivatives Based on Sulfonamide

Abstract

Several new and know sulfonamide Schiff bases were prepared by the condensation reaction of sulfonamide (i.e.2-amino-4chlorobenzenesulfonamide, 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-onederivatives were characterized by IR, 1 H NMR, 13 C 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-onecompounds were tested in vitro against Staphylococcus aureus, Bacillus, Escherichia coli and Pseudomonas aeruginosa. Furthermore, the antioxidant and anticancer efficiency of compounds were evaluated.