INTRODUCTION: Adequate hyperglycemic control is still a huge challenge with the clinically used therapeutics. New, more effective anti-diabetic agents are on the top list of drug discovery projects. METHODS: This article deals with the in vitro anti-diabetic potential of 2, 3 dichloroIndolinone (C1) and 2, 6-dichloroIndolinone (C2) on α-glucosidase and α-amylase followed by in silico analysis. RESULTS: Both compounds, C-1 and C-2, caused significant inhibition of α-glucosidase at various test concentrations with IC CONCLUSION: In short, this study will contribute to providing these compounds with an improved anti-diabetic profile and decreased toxicity.