3-香豆素甲酸乙酯类化合物的制备与抗真菌活性  

Synthesis and Antifungal Activity of the Derivatives of Coumarin-3-formates

作　　者：史晨燕 李浩鹏 刘睿媛 耿会玲 SHI Chen-yan;LI Hao-peng;LIU Rui-yuan;GENG Hui-ling(College of Chemistry and Pharmacy, Northwest A＆F University ,Yangling, Shaanxi 712100 ,China)

机构地区：[1]西北农林科技大学化学与药学院,陕西杨陵712100

出　　处：《西北林学院学报》2018年第3期186-191,共6页Journal of Northwest Forestry University

基　　金：国家自然科学基金(31572038);陕西省农业攻关(2016NY-130);陕西省博士后科学基金(2014-03)

摘　　要：采用Knoevenagel缩合法,在无水乙醇存在下,不同取代水杨醛与丙二酸二乙酯在哌啶催化下发生缩合反应,合成了15个3-香豆素甲酸乙酯类化合物(产率为83%~93%),并对其结构采用~1H NMR、^(13)C NMR和ESI-MS进行了表征。以醚菌酯为阳性对照,采用菌丝线性生长速率法测定了它们对苹果腐烂、苹果轮纹、玉米弯孢等12种植物病源真菌的抑制活性。结果表明,大多数化合物在50μg·mL^(-1)时对供试菌有不同程度的抑制活性;苯环上取代基的引入对其活性均有所提高,而给电子取代基对活性的提高程度高于吸电子取代基。化合物A6对苹果腐烂病原菌的活性最高,其EC50值(65.4μg·mL^(-1))高于阳性对照醚菌酯(84.7μg·mL^(-1)),有进一步研究与开发价值。研究结果为后续开发香豆素类抗菌剂提供了理论依据。In the presence of absolute ethanol,a series of ethyl coumarin-3-formates with a number of 15 were synthesized in 83%-93% yields via piperidine-catalyzed Knoevenagel condensation reaction of substituted salicylaldehyde with diethyl malonate.Their structures were confirmed by the spectra of ~1H NMR,^（13）C NMR and ESI-MS.Their in vitro antifungal activitie against 12 strains of plant pathogenic fungi were tested by the mycelium linear growth rate method.Kresoxim-methyl was used as a positive control.The results showed that most of the compounds displayed the antifungal activity in varying degrees.Introduction of different kinds of groups to the phenyl ring boosted the antifungal activities of corresponding compounds.The activities of compounds with electron-donating groups were higher than those with electronwithdrawing ones.Among them,A6 not only exhibited the highest activity for Valsa mali,but also its EC50 value（65.4μg/mL）was even higher than that of Kresoxim-methyl（84.7μg/mL）,indicating that it was deserved to be further researched and developed.The results of this study would provide theoretical basis for the further development of coumarins fungicides.

关 键 词：3-香豆素甲酸乙酯类化合物 合成 植物病源真菌 抑菌活性 

分 类 号：S482.2[农业科学—农药学]