Diabetes mellitus (DM) is a metabolic condition that is a profound health concern across the globe due to its contribution to the increased mortality rate. It affects millions of people around the world and is associated with severe complications among people diagnosed with it. Among the array of approaches used for the management of DM, inhibition of enzymes viz. α-amylase and α-glucosidase which are responsible for sugars hydrolysis is regarded as a feasible therapeutic protocol for the management of DM. Herein, we report the synthesis of benzylidenehydrazine derivatives as well as their evaluation as α-glucosidase and α-amylase inhibitors including their antioxidant testing. Generally, all the synthesized derivatives were more potent inhibitors of α-amylase than of α-glucosidase. Specifically, 2,4 fluoro substituted analogue 9 (IC