Yang Da-Cheng, Yan Ju-Fang, Xu Jin, Ye Fei, Zhou Zu-Wen, Zhang Wei-Yu, Fan Li, Chen Xin
School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
Yao Xue Xue Bao. 2010 Jan;45(1):66-71.
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.
为寻找新型抗糖尿病先导化合物，通过4-苯基-2-丁酮、磺胺与一些芳香醛的三组分一锅法缩合反应，直接设计并合成了4-(1-芳基-3-氧代-5-苯基戊基氨基)苯磺酰胺，产率为23%-97%。通过1H NMR、13C NMR、FTIR、ESI-MS和HR-MS确定了这12种新型曼尼希碱的化学结构。抗糖尿病活性筛选结果表明，这些目标化合物大多具有α-葡萄糖苷酶抑制活性，其中化合物1e活性最强。化合物11具有良好的过氧化物酶体增殖物激活受体反应元件(PPRE)激动剂活性。还初步探讨了这些含苯磺酰胺单元的新型β-氨基酮的构效关系。
