Novel thiosemicarbazone derivatives were synthesized via condensation reactions between the corresponding thiosemicarbazides and 4-(methylsulfonyl)acetophenone. The chemical structures of all compounds were elucidated by infrared (IR), ¹H-NMR and ¹³C-NMR spectroscopy and mass spectrometry. Antioxidant studies of all compounds were performed by using CUPRAC, FRAP, DPPH methods. 2-{1-[4-(Methylsulfonyl)phenyl]ethylidene}-N-phenylhydrazinecarbothioamide (1) possessed good antioxidant activity with an SC₅₀ value of 15.70 µM which also is higher than standard drug, ascorbic acid. All compounds were evaluated for their antidiabetic properties as α-glycosidase and α-amylase inhibitors. Compound 1 was found to be the most active compound against α-glucosidase and α-amylase with IC₅₀ values of 1.58 µM and 3.24 µM, respectively. The enzyme kinetic studies demonstrated that compound 1 has a competitive mode of binding. Furthermore, molecular docking studies have elucidated the binding mechanism at the molecular level by examining the molecular interactions between compound 1 and these enzymes. Graphical Abstract