In the process of a search for new compounds to reduce hyperglycemia by α-amylase and α-glucosidase enzyme inhibition, a series of imidazole appended phenoxyquinoline derivatives were synthesized. Initially, 2-cholo-3-formyl quinoline 3 was treated with various substituted phenol in the presence of K₂CO₃ in DMF to get 2-phenoxyquinoline-3-carbaldehyde which in turn was treated with o-phenylenediamine to afford the corresponding 3-(1H-benzo[d]imidazol-2-yl)-2-phenoxyquinolines (7a–j). All the synthesized compounds were evaluated for their in vitro and in silico α-amylase and α-glucosidase inhibitory activity using acarbose as a standard. Among the tested compounds, compound 7a was found to exhibit a potent binding affinity; and inhibitory activity (80.90% and 76.26%) with corresponding IC₅₀ values of 104.30 ± 3.31 μmol/mL and 135.67 ± 2.80 μmol/mL toward α-amylase and α-glucosidase, respectively.