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The reaction of 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3 H )-thione  3  with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding  N -Mannich bases 3-arylaminomethyl-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3 H )-thiones  4a – l  or 3-[(4-substituted piperazin-1-yl)methyl]-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3 H )-thiones  5a – d , respectively. The in vitro inhibitory activity of compounds  4a – l  and  5a – d  was assessed against pathogenic Gram-positive, Gram-negative bacteria, and the yeast-like pathogenic fungus  Candida albicans . The piperazinomethyl derivatives  5c  and  5d  displayed broad-spectrum antibacterial activities the minimal inhibitory concentration (MIC) 0.5–8 μg/mL) and compounds  4j ,  4l ,  5a,  and  5b  showed potent activity against the tested Gram-positive bacteria. In addition, the anti-proliferative activity of the compounds was evaluated against prostate cancer (PC3), human colorectal cancer (HCT-116), human hepatocellular carcinoma (HePG-2), human epithelioid carcinoma (HeLa), and human breast cancer (MCF7) cell lines. The optimum anti-proliferative activity was attained by compounds  4l ,  5a ,  5c,  and  5d .

1,3,4-Oxadiazole N-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities