title: [Synthesis and investigation on antidiabetic activity of 4-(1-aryl-3-oxo-5-phenylpentylamino) benzenesulfonamide].
abstract: 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 alpha-glucosidase inhibitory activity, among which compound le is the strongest one. And compound 11 possesses good peroxisome proliferator-activated receptor response element (PPRE) agonist activity. The structure-activity relationship of these new beta-amino ketones containing benzenesulfonamide unit was also discussed preliminarily.
authors.affiliation: School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China. hxydc@swu.edu.cn
authors.forename: Da-Cheng
authors.initials: DC
authors.lastname: Yang
authors.forename: Ju-Fang
authors.initials: JF
authors.lastname: Yan
authors.forename: Jin
authors.initials: J
authors.lastname: Xu
authors.forename: Fei
authors.initials: F
authors.lastname: Ye
authors.forename: Zu-Wen
authors.initials: ZW
authors.lastname: Zhou
authors.forename: Wei-Yu
authors.initials: WY
authors.lastname: Zhang
authors.forename: Li
authors.initials: L
authors.lastname: Fan
authors.forename: Xin
authors.initials: X
authors.lastname: Chen
mesh_terms: D015195:Drug Design; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047492:Peroxisome Proliferator-Activated Receptors / Q000819:agonists*; D013329:Structure-Activity Relationship; D000077145:Sulfanilamide; D013424:Sulfanilamides / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000520:alpha-Glucosidases / Q000378:metabolism*; D000096926:Benzenesulfonamides
chemical_list: D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D047492:Peroxisome Proliferator-Activated Receptors; D000077145:Sulfanilamide; D013424:Sulfanilamides; D013449:Sulfonamides; D000520:alpha-Glucosidases; D000096926:Benzenesulfonamides