The synthesized 3,3-di(indoloyl)indolin-2-ones 1a - p showed desired higher α-glucosidase inhibitory activities and lower α-amylase inhibitory activities than standard drug acarbose. Particularly, compound 1i showed favourable higher α-glucosidase % inhibition of 67±13 and lower α-amylase % inhibition of 51±4 in comparison to acarbose with % inhibition activities of 19±5 and 90±2, respectively. Docking studies of selected 3,3-di(indoloyl)indolin-2-ones revealed key interactions with the active sites of both α-glucosidase and α-amylase, further supporting the observed % inhibitory activities. Furthermore, the binding energies are consistent with the % inhibition values. The results suggest that 3,3-di(indoloyl)indolin-2-ones may be developed as suitable Alpha Glucosidase Inhibitors (AGIs) and the lower a-amylase activities should be advantageous to reduce the side effects exhibited by commercial AGIS.