Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids

doi:10.6023/cjoc201701030

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

Notes

取代黄酮磷酸酯的合成及抗细菌活性研究

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

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 E-mail:wxue@gzu.edu.cn
基金资助:
国家自然科学基金（No.21462012）和贵州省优秀青年科技人才（No.201535）资助项目.

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

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 E-mail:wxue@gzu.edu.cn
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).

1. Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids.PDF(7477KB)

Abstract

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

Cite this article

Huang Minguo, Ruan Xianghui, Zhang Juping, Li Qin, Wang Yihui, Chen Lijuan, Zhang Cheng, Li Pu, Xue Wei. Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids[J]. Chin. J. Org. Chem., 2017, 37(8): 2145-2152.

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取代黄酮磷酸酯的合成及抗细菌活性研究

Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids

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