A series of all novels 4(3-(4-Fluorophenyl)2-methyl-1-(4-(sulfonamidesubtituted)phenyl)-4-oxoazitidin-2-yl)-3-methyl-1-(p-tolyl)-1H-pyrazol-5(4H) One 5a-5r poly functionalized derivatives were containing sulfonamide functionality united with 2-Azitidinone (Azitidin-2-one or β-lactam) group which designed and synthesized with moderate to good yield. The starting with 4-acyl-2-pyrazolin-5-one (APYZ) 1 which condensed with different sulfonamides 2 produced intermediate Schiff bases 4-(arylideneamino)-N-(thiazol-2-yl)benzensulfonamide 3a-r were cyclization with 2-(4-flourophenyl)chloroacetylchloride (F-CAC) 4 which produced targeted compounds 5a-5r of 2-Azitidinone versatile group in good yield. The isolated compounds were recognized by spectral and elemental investigation. The compounds 5f, 5l, 5n, and 5r showed excellent increased antibacterial activity compared to streptomycin standard drug and 5c, 5f, 5l, 5o, and 5r showed moderate to good antioxidant properties with used DPPH radical scavenging assay.