A novel 4-[(8-hydroxyquinolin-5-yl)methyl]aminobenzenesulfonamide (HQMABS) was synthesized by optimized reaction of 4-aminobenzenesulfonamide with 5-chloromethyl-8-hydroxyquinoline hydrochloride (CMHQ). Various oxinates of HQMABS were also prepared using Mn(II), Fe(II), Co(II), Ni(II), Cu(II), and Zn(II) metal salts. All compounds were analyzed by physicochemical, thermogravimetric and spectroscopic techniques. Antimicrobial activity was carried out using agar-plate method against various strains of bacteria (Staphylococcus aureus, Bacillus subtillis, Pseudomonas aerugionsa, and Escherichia coli) and spores of fungi (Aspergillus niger and Aspergillus flavous). The results showed significantly higher antimicrobial activity of HQMABS compared to the parent 8-hydroxyquinoline and sulfonamide, while oxinates of HQMABS showed milder activity.