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有机化学
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有机化学 ›› 2017, Vol. 37 ›› Issue (8): 2145-2152.DOI: 10.6023/cjoc201701030 上一篇    下一篇

研究简报

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   

  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 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   

  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 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).

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将取代黄酮醇引入亚磷酸二乙酯，设计合成了14个含取代黄酮基磷酸酯类新化合物，通过1H NMR，13C NMR，31P NMR，MS，IR和HRMS对它们的结构进行了表征.采用浊度法测试了目标化合物的离体抑菌活性，表明部分目标化合物在100 μg/mL浓度下对水稻白叶枯病菌表现出良好的抑制率，明显优于对照药剂噻菌铜和叶枯唑（≥57.4%）.其中O，O'-二乙基-O"-（2'，7-二甲氧基黄酮-3-基）磷酸酯（2b）、O，O'-二乙基-O"-（2'-甲氧基-7-乙氧基黄酮-3-基）磷酸酯（2f）和O，O'-二乙基-O"-（3'，4'-二甲氧基-7-乙氧基黄酮-3-基）磷酸酯（2m）在100 μg/mL浓度下对水稻白叶枯病菌的抑制率分别达到92.8%，87.7%和88.3%.O，O'-二乙基-O"-（4'-氟-7-乙氧基黄酮-3-基）磷酸酯（2h）和O，O'-二乙基-O"-（4'-甲基-7-乙氧基黄酮-3-基）磷酸酯（2k）在100 μg/mL浓度下对柑橘溃疡病菌也有较好的抑制活性，其抑制率分别为85.1%和71.7%.

关键词: 亚磷酸酯, 黄酮醇, 黄酮磷酸酯衍生物, 抗细菌活性

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