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Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236mg/dl) compared to pioglitazone and rosiglitazone (230 and 263mg/dl, respectively). Also chalcones with iodo substitution at position 3 on A-ring were comparably active (⩽238mg/dl). The structure–activity relationship of the tested chalcones was studied and the findings were supported statistically