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以对氨基苯乙酸为起始原料,采用氨基磺酰化、羧基酯化、酰胺脱脂肪酰基及氨基酰基化等方法,经多条路线合成得到6个中间体和20个含有苯磺酰胺和对氨基苯乙酸结构单元的目标分子,24个新分子的结构经1H NMR、13C NMR和HR-MS证实。体外过氧化物酶体增殖物激活受体(PPAR)激动活性初步筛选结果显示,多数分子的PPAR相对激动活性不强,但有4个化合物的PPAR相对激动活性超过58%,其中TM2-i达到81.79%。由此首次发现,含有苯磺酰胺和对氨基苯乙酸结构单元的某些化合物具有潜在抗糖尿病活性。本研究还发现,SOCl2/醇体系可一步实现烷基羧酸的酯化和N-苯基脂肪酰胺脱酰基化,为某些酯基和酰胺基共存分子的选择性反应提供了新方法。
Using p-aminophenylacetic acid as the starting material, six intermediates and twenty intermediates containing benzenesulfonamide and p-aminobenzamide were synthesized by aminosulfonylation, carboxyl esterification, amide de-fatty acyl and aminoacylation. The target molecule of aminophenylacetic acid structural unit, the structure of 24 new molecules was confirmed by 1H NMR, 13C NMR and HR-MS. The results of in vitro PPAR agonistic screening showed that the relative activation of PPAR was not strong in most of the molecules, but the relative activation of PPAR was over 58% in four of the four compounds, of which TM2-i reached 81.79%. It was first discovered that certain compounds containing benzenesulfonamide and p-aminophenylacetic acid units have potential anti-diabetic activity. The present study also found that the SOCl2 / alcohol system can be one-step esterification of alkyl carboxylic acids and N-phenyl-fatty acid amide deacylation, for some selective reaction of ester and amide-based molecules provided a new method.