학술논문
新型1-(4-取代苯基)-3-[4-(4-氧香豆素基)苯基]硫脲衍生物的合成及其抑菌活性 / Synthesis and Antibacterial Activities of Novel 1-(4-Substitutedphenyl)-3-{4-[(2-oxo-2H-chromen-4-yl)oxy]phenyl}thiourea Derivatives
Document Type
Academic Journal
Source
合成化学 / Chinese Journal of Synthetic Chemistry. 25(3):190-212
Subject
Language
Chinese
ISSN
1005-1511
Abstract
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86.90 μg·mL-1,优于噻菌铜(130.25 μg·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82.48 μg·mL-1,优于噻菌铜(123.94 μg·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 by 1H NMR, 13C 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).
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 by 1H NMR, 13C 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).