摘要
以4-羟基香豆素为原料,经氯化、醚化和异硫氰酸化3步反应制得中间体——4-(4-异硫氰酸酯苯氧基)香豆素(3);3与取代芳香胺经加成反应合成了9个新型的1-(4-取代苯基)-3-[4-(4-氧香豆素基)苯基]硫脲衍生物(4a^4i),其结构经1H NMR,13C NMR,IR和MS(ESI)表征。采用浑浊度法测试了4的抑菌活性。结果表明:4a、4b、4e和4f抑制烟草青枯菌活性EC50值分别为112.02、121.39、88.72和86.90μg·mL^(-1),优于噻菌铜(130.25μg·mL^(-1));4a、4b、4e和4f抑制番茄青枯菌活性EC50值分别为107.89、110.69、82.43和82.48μg·mL^(-1),优于噻菌铜(123.94μg·mL^(-1))。
The intermediate,4-(4-isothiocyanatophenoxy)-2H-chromen-2-one(3) was synthesized from 4-hydroxycoumarin via chloride,etherification,and isothiocyanate reactions. Nine novel 1-(4-substitutedphenyl)-3-{ 4-[(2-oxo-2H-chromen-4-yl) oxy]phenyl } thiourea derivatives(4a - 4i) were obtained by the addition reaction of 3 with substituted aromatic amines. The structures were characterized by1 H NMR,13 C NMR,IR and MS(ESI). Antibacterial activities of 4 against Xanthomonas oryzae pv. oryzae(Xoo) and Xanthomonas citri subsp. Citri(Xcc) were evaluated by the turbidimeter test. The results indicated that 4a,4b,4e and 4f showed excellent antibacterial activities against Xoo with EC50 of 112. 02,121. 39,88. 72 and 86. 90 μg·mL^-1,respectively,which were better than that of thiodi-azole-copper(130. 25 μg·mL^-1). 4a,4b,4e and 4f showed excellent antibacterial activities against Xcc with EC50 of 107. 89,110. 69,82. 43 and 82. 48 μg·mL^-1,respectively,which were better than that of thiodiazole-copper(123. 94 μg·mL^-1).
作者
陈美航
王晓斌
吴文能
CHEN Mei-hang WANG Xiao-bin WU Wen-neng(Material and Chemistry Engineering Institution, Tongren College, Tongren 554300, China Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, China Food and Pharmaceutical Engineering Institution, Guiyang College, Guiyang 550005, China)
出处
《合成化学》
CAS
CSCD
2017年第3期190-194,212,共6页
Chinese Journal of Synthetic Chemistry
基金
贵州省科学技术资金资助项目([2011]2080
[2016]1006)
铜仁学院博士基金资助项目(trxyD H1618)
关键词
香豆素
硫脲类衍生物
合成
抑菌活性
coumarin
thiourea derivative
synthesis
antibacterial activity