In the search of heterocyclic ring systems potentially useful as α-glucosidase inhibitors we have synthesized a set of heterocycles bearing hydroacridone 4-5, hydroxanthone 6, quinazolone 8, benzoyl phtalimide 9 and isoquinolone 10-11. These compounds under study were subjected to enzyme inhibition and compared against reference inhibitor acarbose observing potent inhibition for benzoyl phtalimide 9, and isoquinolone dione 11. Based on their inhibition activity, both candidates were selected for docking analysis to determine their best posing, and the interactions involved between the ligand and the residues. A comparative analysis was established to determine the potential correlation between the interactions found, the inhibition observed for the candidates and the interactions observed for the reference inhibitor acarbose.