Chinese Journal of Organic Chemistry >
Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids
Received date: 2017-01-14
Revised date: 2017-02-28
Online published: 2017-04-18
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.
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]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2145 -2152 . DOI: 10.6023/cjoc201701030
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