The de novo approach to rational drug design provides a powerful tool for the construction from smaller compounds of entirely novel molecules that satisfy a set of user-defined constraints such as shape and electrostatic complementarity to a protein binding site. Various heuristics (such as predicting bioactivity score and synthetic accessibility) have to be adopted to evaluate and prune large answer sets with the goal of suggesting ligands with high bioactivity score but low structural complexity, the complexity analysis technique being implemented within the Mol inspiration software. This de novo design system is based on the bioactivity score and molecular properties of various heterocyclic topologies and atom substitution patterns in existing drugs and commercially available starting materials. Type 2 diabetes is accompanied both by impaired insulin secretion and by insulin resistance and metabolic disorders of fats and carbohydrates. The UK Prospective Diabetes Study (UKPDS) and Diabetes Control and Complications Trial (DCCT) have established that complications in type 1 and 2 patients are clearly linked to elevated blood glucose levels. Different hetero cyclic moieties were incorporated with the lead in different positions and their molecular properties which satisfy the Lipinski’s rule were calculated. Indole is a drug like scaffold and is also a core skeleton for the active sites involved in enzyme inhibition in diabetes. It offers a promising approach for the development of newer drugs for the treatment of type 2 diabetes and the associated metabolic syndromes which include obesity, hypertension, and dyslipidemia. By using de novo drug designing approach and mol inspiration software tool and to prepare derivatives of Triazole incorporated with indole ring system and screen the synthesized compounds for their α – amylase and α –Glucosidase inhibitory actions which will indicate their capacity to induce hypoglycemia.