Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2145-2152.DOI: 10.6023/cjoc201701030 Previous Articles     Next Articles



黄民国, 阮祥辉, 张菊平, 李琴, 王一会, 陈丽娟, 张橙, 李普, 薛伟   

  1. 贵州大学精细化工研究开发中心 绿色农药与农业生物工程国家重点实验室培育基地 教育部绿色农药与农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2017-01-14 修回日期:2017-02-28 发布日期:2017-04-18
  • 通讯作者: 薛伟
  • 基金资助:


Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids

Huang Minguo, Ruan Xianghui, Zhang Juping, Li Qin, Wang Yihui, Chen Lijuan, Zhang Cheng, Li Pu, Xue Wei   

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2017-01-14 Revised:2017-02-28 Published:2017-04-18
  • Contact: 10.6023/cjoc201701030
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21462012) and the Excellent Young Talents of Science and Technology in Guizhou Province (No. 201535).

By introducing flavonoids group into H-phosphonate, fourteen novel phosphonate derivatives containing flavonoid unit were designed and synthesized. Their structures were characterized by 1H NMR,13C NMR, 31P NMR, MS, IR and HRMS, and their antibacterial activities were evaluated via turbidimeter test in vitro. The bioassays results reveal that part of the target compounds exhibit better activities against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac) than positive controls thiodiazole copper and bismerthiazol (≥57.4%). Among them, the inhibitory rates of (2-(2-methoxyphenyl)-7-methoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2b), (2-(2-methoxyphenyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2f) and (2-(3,4-dimethoxyphenyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2m) reached 92.8%, 87.7% and 88.3% against Xoo at a concentration of 100 μg/mL, respectively. In addition, the inhibitory rates of (2-(4-fluorophenyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2h) and (2-(p-tolyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2k) reached 85.1% and 71.7% against Xac at a concentration of 100 μg/mL, respectively.

Key words: H-phosphonate, flavonol, phosphonate derivatives containing flavonoid, antibacterial activity