Synthesis and investigation on antidiabetic activity of 4-(1-aryl-3-oxo-5-phenylpentylamino) benzenesulfonamide

Searching for new antidiabetic lead compound, 4-(1-aryl-3-oxo-5-phenylpentylamino) benzenesulfonamides were designed and synthesized directly by three component one-pot condensation of 4-phenyl- 2-butanone and sulfanilamide with some aromatic aldehydes at an yield of 23%−97%.  The chemical structures of the twelve new Mannich bases were confirmed by ¹H NMR, ¹³C NMR, FTIR, ESI-MS and HR-MS.  The screening results of antidiabetic activity indicated that most of these title compounds possess α-glucosidase   inhibitory activity, among which compound 1e is the strongest one.  And compound 1l possesses good peroxisome proliferator-activated receptor response element (PPRE) agonist activity.  The structure-activity relationship of these new β-amino ketones containing benzenesulfonamide unit was also discussed preliminarily.