The newly synthesized Mannich bases were characterized in this study on the basis of UV–Vis, FT-IR, 1 H NMR, 13C NMR, Mass spectroscopic techniques, and micro elemental analyses. The single crystal X-ray diffraction analysis on one of the Mannich bases 1-[anilino(phenyl)methyl] pyrrolidine-2,5-dione was also carried out. This compound crystallizes in the monoclinic system, space group P21/c, with a = 15.4871(8) A˚ , b = 6.6637 (3) A˚ , c = 20.1544 (11) A˚ , b = 109.403(2), Z = 4 and V = 1961.83 (17) A˚ 3 . Antibacterial study has been carried out on all the Mannich bases against a panel of antibacterial (Escherichia coli, Salmonella typhi, and Bacillus subtilis) and antifungal agents (Aspergillus oryzae and Aspergillus fumigates), using Penicillin, Streptomycin, and Amphotericin B as standards. The antioxidant activities of the Mannich bases were determined by measuring their reducing power, their ability to inhibit linoleic acid peroxidation, and 2,2-diphenyl-picrylhydrazyl (DPPH)'s radical scavenging activities. The synthesized compounds contain moderate antioxidant and antimicrobial activities.