In this study, a series of salicylic acid derivatives were designed and synthesized as novel non-saccharide α-glucosidase inhibitors. Biological evaluation indicated that when compared to acarbose, compounds T9 , T10 , and T32 exhibited a higher potency of α-glucosidase inhibitory activity with IC₅₀ values of 0.15 ± 0.01, 0.086 ± 0.01 and 0.32 ± 0.02 mM, respectively. Evaluation of the inhibition kinetics indicated that T9 , T10 , T32 , and acarbose interacted with α-glucosidase in a mixed non-competitive inhibitory manner. Moreover, T9 , T10 , and T32 statically quenched the fluorescence of α-glucosidase by formation of an inhibitor-α-glucosidase complex. The docking results showed that hydrogen bonds were generated between the test compounds and α-glucosidase. The antioxidant study revealed that compound T10 exhibited a higher antioxidant activity via scavenging 1,1-diphenyl-2-picrylhydrazyl free radical ( DPPH ), thereby inhibiting lipid peroxidation and the total reduction capacity. In brief, the salicylic acid derivatives identified in this study were promising candidates for development as novel non-saccharide α-glucosidase inhibitors.