In this study, four compounds of 2-(phenylthio)-ethyl benzoate derivatives were synthesized and evaluated for their antitumor, antibacterial, and antifungal activities. These compounds were characterized and evaluated for their cytotoxic activity in MCF-7-human carcinoma cells that showed a significant decrease for compounds 2a–2d in the average of G2-M phase as 8.13 ± 1.4, 10.66 ± 1.5, 14 ± 2.2, and 3.66 ± 0.8%, respectively, compared with untreated cells (21 ± 2%; p < 0.05). The data suggest that 2d compound could have an anticancer potential in the G2-M phase arrest of MCF-7 cells ultimately leading to necrosis. The compounds were tested for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia, Proteus vulgaris, Enterococcus faecium, Pseudomonas aeruginosa, MRSA, and Candida albicans and showed antimicrobial potential with MIC value average (3.125–6.25 mg/ml), compared with ampicillin (0.001–3.125 mg/ml). When the MIC of the four compounds was compared with known references, we found that the 2a compound has the same MIC as fluconazole (1.56 mg/ml), inhibitor of Candida growth. Moreover, 2a, 2b,, and 2d have the same MIC as ampicillin (3.125 mg/ml) for the inhibition of S. aureus.