A series of novel isolated β-lactams 3a-c and thiazolidinone derivatives 4a-c were successfully synthesized from reactions of new Schiff's bases 2a-c with chloroacetyl chloride and thioglycolic acid. The chemical structures of the new compounds were confirmed through different spectroscopic techniques including IR, 1H and 13C NMR, mass spectrometry and elemental analysis. The antimicrobial activity of the obtained compounds was assessed in vitro against gram-positive Staphylococcus aureus and gram-negative Escherichia coli bacteria and Aspergillus flavus and Candida albicans fungi. All compounds exhibited good to excellent antimicrobial activity against the tested strains. Furthermore, a molecular docking study was carried out for the synthesized compounds and the results indicated that compounds 3b and 4b display comparable binding affinity scores as that of glutamate. These two compounds are promising candidates as antibacterial and antifungal agents that would deserve further investigations.