In this investigation, we investigated the inhibitory effects of several indole-based compounds on the activity of intestinal and pancreatic alpha-glucosidase. It appears that antidiabetic medications must contain enzyme inhibitors that block the breakdown of carbohydrates. All analogues had good to moderate inhibitory interactions with alpha-glucosidase (IC50 = 3.08 to 7.37) compared to conventional acarbose (IC50 = 12.18). The activity potential for both enzyme inhibitory interactions and the analogues 3, 4, 6, 10, 12 and 16 were good. In order to suggest the impact of substituents on the inhibitory potential of analogues, structure activity relationships were carefully considered. Additional possible analogues and the enzyme active site interacted, according to docking studies.