The present study comprised of the synthesis of dicyanoaniline derivatives of pyridine, thiophene, furan, and substituted phenyl 1 – 29 . All synthetic derivatives were evaluated for their potential to inhibit α -amylase and α -glucosidase enzymes. The synthesized compounds are classified into three categories A, B, and C based on variable substituents at R 1 and R 2, and the structure–activity relationship was discussed accordingly. Amongst twenty-nine derivatives, 1 – 29 , five compounds 2 , 9 , 18 , 23 , and 24 displayed excellent inhibition against α -amylase and α -glucosidase enzymes with the IC 50 values ranging between 20.33 ± 0.02–25.50 ± 0.06 µM and 21.01 ± 0.12–27.75 ± 0.17 µM, respectively, while other compounds showed moderate to weak inhibition against both enzymes. Acarbose was used as the positive control in this study. The enzyme kinetic studies showed non-competitive and un-competitive types of inhibition mechanism against α -amylase and α -glucosidase enzymes, respectively. In silico studies have demonstrated the involvement of these molecules in numerous binding interactions within the active site of the enzyme.