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Type 2 diabetes mellitus is a progressive disease that affects almost 8.3% of global population. Regardless the availability of vast variety of oral hypoglycemics, only 36% of patients achieves proper glycemic control. With the advantage of low risk of hypoglycemia, DPP-IV attracted the attention of medicinal chemists as a new target for oral hypoglycemics. In this report, a lead compound 1, with antipyrine scaffold, was obtained, and its binding mode was calculated. Several derivatives with bridged nitrogenous heterocycles have been synthesized via multi-component reaction under controlled microwave heating conditions. The antidiabetic activity vs. DPP-IV protein was evaluated and compared with sitagliptin. Compounds with small or medium sized nitrogenous bridges were comparable with sitagliptin in term of DPP-IV inhibitory activity, potentially via targeting Glu203 and Glu204. The oral hypoglycemic activities of compounds with submicromolar IC50 values were further evaluated using diabetic mouse model.