Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (04): 582-589. Previous Articles     Next Articles

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  1. (1西南大学化学化工学院 重庆 400715)
    (2成都地奥制药集团药物筛选中心 成都 610041)
  • 收稿日期:2009-08-24 修回日期:2009-11-25 发布日期:2010-04-28
  • 通讯作者: 杨大成

Synthesis and Preliminary Evaluation of Antidiabetic Activity for β-Amino Ketone Containing Isoxazole Moiety

Zhou Zuwen1 Yan Jufang2 Tang Xuemei1 Zhang Weiyu2 Zhang Yingxia1 Chen Xin2 Su Xiaoyan1 Yang Dacheng*,1   

  1. (1 School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715)
    (2 Chengdu Di Ao Pharmaceutical Group, Chengdu 610041)
  • Received:2009-08-24 Revised:2009-11-25 Published:2010-04-28

In order to find highly active antidiabetic compounds, fifteen new β-amino ketones containing a isoxazole moiety were synthesized directly through Mannich reaction with facile method and mild reaction condition in the yields of 51.2%~89.3%. Their structures were confirmed by 1H NMR, 13C NMR, ESI MS and HR MS techniques. Preliminary bioassay indicated that although most of these compounds possess weak α-glucosidase inhibitory activity and protein tyrosine phosphatase 1B inhibitory activity in low concentration, some could activate peroxisome proliferator-activated receptors (PPAR) response element moderately. Compound 1-(3,4-dichlorophenyl)-3-(6-methoxynaphthalen-2-yl)-3-(5-methylisoxazol-3-ylamino)propan- 1-one (15) has the strongest activity (75.3%), which deserved further study. The reaction conditions and the structure-activity relationship of these compounds were also discussed in this paper.

Key words: diabetes mellitus, isoxazole, β-amino ketone, Mannich reaction