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

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100μg/m L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100μg/m L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100μg/m L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%.

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,13 C NMR, 31 P 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/m L, 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/m L, respectively.