The in vitro anti-diabetes and anti-inflammatory inhibitory activities of the synthesized 2-formylphenyl sulfonates and their hydrazone derivatives were evaluated through enzymatic assays as potential α-glucosidase and lipoxygenase (LOX-15) inhibitors. The preliminary inhibitory results obtained, revealed that the prepared compounds are good inhibitors of α-glucosidase as compared to lipoxygenase (LOX-15). Compounds 2 g and 3 h were found to exhibit significant inhibitory activities against α-glucosidase with IC50 values of 3.1 µM and 2.6 µM, respectively. Moderate inhibitory activity was also observed for compound 3a (IC50 = 7.3 µM) against this enzyme. Enzyme kinetics studies of the most active compound (3 h) suggested a mixed mode of inhibition for this compound against α-glucosidase. The molecular docking and molecular dynamics simulation of compounds 2 g, 3a and 3 h into the active sites of α-glucosidase were used to predict the binding modes and structure activity relationship for these compounds. The molecular dynamics simulation demonstrated that compound 3 h significant inhibitory activity is due to its ability to bind to both the catalytic and secondary sites of the enzyme.