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新型香豆素噻唑衍生物的合成及其抑菌活性

Synthesis and Antifungal Activity of Novel Coumarin Thiazole Derivatives

  • 摘要: 为了得到更高杀菌活性的香豆素噻唑衍生物,以7-羟基香豆素为原料,对其羟基进行改造,合成了13个香豆素噻唑衍生物8a-8m。采用核磁共振氢谱(1H NMR)、碳谱(13C NMR)对合成化合物的结构进行了表征。通过生长速率法测定了合成化合物对芝麻致病真菌(菜豆壳球孢、尖孢镰刀菌和多主棒孢)的抑菌活性。结果表明:在质量浓度为500μg/mL下,合成化合物均有一定的抑菌活性。其中,N-(4-(3,4-二氯苯基)噻唑-2-基)-2-(2-氧代-香豆素-7-基氧基)乙酰胺(8a)对菜豆壳球孢的抑制活性优于对照药烯酰吗啉,对尖孢镰刀菌和多主棒孢的抑制活性与烯酰吗啉相当;N-(4-(4-噻吩-2-基)噻唑-2-基)-2-(2-氧代-香豆素-7-基氧基)乙酰胺(8k)对菜豆壳球孢的抑制活性接近对照药。

     

    Abstract: In order to find coumarin thiazole derivatives with high antifungal activity, thirteen coumarin thiazole derivatives 8a-8m which have not been reported in literature were synthesized by using 7-hydroxycoumarin as raw material and modifying hydroxyl group. The structures of the products were characterized by ~1H NMR and 13C NMR. The growth rate method was used to determine the antifungal activity of the compound against the pathogenic fungi of sesame: Macrophomina phaseolina, Fusarium oxysporum and Corynespora cassiicola. The results show that all the compounds have certain antifungal activity at the concentration of 500 μg/mL. Among them, the inhibitory activity of N-(4-(3, 4-dichlorophenyl) thiazol-2-yl)-2-(2-oxy-coumarin-7-methoxy) acetamide(8a) is better than dimethomorph against Macrophomina phaseolina, and is equivalent to dimethomorph against Fusarium oxysporum and Corynespora cassiicola. N-(4-(4-thiophen-2-l) thiazol-2-l)-2-(2-oxy-coumarin-7-methoxyxy) acetamide(8k) is close to the control drug in inhibiting the activity of the Macrophomina phaseolina.

     

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