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

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Abstract

The synthesis of two series of β-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 1H NMR, 13C NMR, ESI-MS and HR-MS. Subsequently, their antidiabetic activities were screened in vitro. The α-glucodase inhibition (α-GI) activity of compound 1e 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 unprecedentedly high PPAR of 130.91%. The structure-activity relationships of the compounds were established. 2i is also subject to further in-depth investigation.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China

    GuangXia Tang, Li Fan, Jin Xu, XiaoLi Song & DaCheng Yang

  2. Drug Screening Center, Chengdu Di Ao Pharmaceutical Group Co., Ltd., Chengdu, 610041, China

    JuFang Yan

  3. Schlumberger Technology Corporation, 110 Schlumberger Drive, Sugar Land, TX, 77478, USA

    Li Jiang

  4. School of Life Science, Southwest University, Chongqing, 400715, China

    LingFei Luo

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  1. GuangXia Tang
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Tang, G., Yan, J., Fan, L. et al. Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities. Sci. China Chem. 56, 490–504 (2013). https://doi.org/10.1007/s11426-012-4816-2

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