Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 1113-1118.DOI: 10.6023/cjoc201211038 Previous Articles     Next Articles



杨家强a, 谷晴a, 束波b, 宋宝安c, 刘静姿a   

  1. a 遵义医学院药学院 遵义 563003;
    b 遵义医学院生物化学与分子生物学教研室 遵义 563003;
    c 贵州大学精细化工研究中心 贵阳 550025
  • 收稿日期:2012-11-20 修回日期:2012-12-20 发布日期:2013-01-07
  • 通讯作者: 杨家强,
  • 基金资助:

    国家自然科学基金(No. 81160385)和贵州省科技厅基金(No. 黔科合J字LKZ[2010]47)资助项目.

Synthesis and Antitumor Activity of O,O'-Dialkyl-α-phenyl-α-(substituted benzoylanoxy)-methylphosphonate

Yang Jiaqianga, Gu Qinga, Shu Bob, Song Baoanc, Liu Jingzia   

  1. a School of Pharmacy, Zunyi Medical College, Zunyi 563003;
    b Department of Biochemistry and Molecular Biology, Zunyi Medical College, Zunyi 563003;
    c Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2012-11-20 Revised:2012-12-20 Published:2013-01-07
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 81160385) and the Science and Technology Department of Guizhou Province (No. LKZ[2010]47).

In search of more effective anticancer agents, the title compounds were prepared via the esterification reaction of α-hydroxyphosphonate and substituted bezoic acid with N,N'-dicyclohexylcarbodiimide (DCC) as condensing agent. Twelve of them were reported for the first time. Their structures were clearly established by elemental analysis, IR, 1H NMR and 13C NMR spectra. The antitumor activities of target compounds were tested for the first time. The result indicated that they exhibited certain antitumor activities, and compounds 2i, 2k, 2m showed more potent activities against SGC-7901 with IC50 values of 18.8, 18.5 and 24.5 μmol/L, against A-549 with IC50 values of 24.1, 29.0 and 20.7 μmol/L. Meanwhile, preliminary structure-activity relationships of the title compounds were studied.

Key words: α-hydroxyphosphonate, synthesis, esterification, antitumor activity