Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities

• Published in: Science China. Chemistry Vol. 56; no. 4; pp. 490 - 504
• Main Authors: Tang, GuangXia, Yan, JuFang, Fan, Li, Xu, Jin, Song, XiaoLi, Jiang, Li, Luo, LingFei, Yang, DaCheng
• Format: Journal Article
• Language: English
• Published: Heidelberg SP Science China Press 01.04.2013; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Ketones; Mannich反应; Molecular structure; NMR; Nuclear magnetic resonance; Synthesis; 合成; 对氨基苯甲酸; 抗糖尿病; 活性化合物; 评价; 过氧化物酶体增殖物激活受体; 部分和; β-amino ketone; α-glucosidase; diabetes mellitus; peroxisome proliferator-activated receptor; Mannich reaction
• ISSN: 1674-7291; 1869-1870
• DOI: 10.1007/s11426-012-4816-2

The synthesis of two series of [3-amino ketones containing a p-aminobenzoic acid moiety （TM.1 and TM-2） using a modified protocol of the Mannich reaction is reported. The molecular structures of a total of tweenty three new target compounds were characterized by ~H NMR, 1~C NMR, ESI-MS and HR-MS. Subsequently, their antidiabetic activities were screened in vitro. The c~-glucodase inhibition （c~-GI） activity of compound le reached a remarkable level of 66.50%. The peroxisome proliferator- activated receptor （PPAR） relative activation activities of six compounds are above 80%, and in particular 2i displays an un- precedentedly high PPAR of 130.91%. The structure-activity relationships of the compounds were established. 2i is also sub- ject to further in-depth investigation.