A series of title compounds, 4-hydroxy-3-(2-substituted-2-thioxoethyl)-1-phenyl/methylquinolin-2(1H)- ones were synthesized and purity of the compounds was ascertained by TLC. The structures of the synthesized compounds were characterized by IR, NMR (1HNMR and 13CNMR) and mass spectral data. Molecular docking studies of the compounds were carried out using Molegro Virtual Docker. All the synthesized compounds were evaluated for anticancer activity against two different cell lines: K562 (leukemia) and A549 (lung cancer) and antibacterial evaluation was also carried out against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Compound (II-a1) showed MIC of 1 μg/mL against B. subtilis and 4 μg/mL against S. aureus. Compound ( II-b1) showed MIC of 4 μg/mL against B. subtilis and 2 μg/mL against S. aureus gram positive bacterial strains. Compound II-a2 showed anticancer activity with IC50 value = 0.765 μM/mL against K562 cell line (leukemia) and II-a3 with IC50 value = 0.774 μM/mL.