摘要/Abstract

设计合成了29个查尔酮衍生物，并用IR、¹H NMR、¹³C NMR和HRMS对其结构进行了表征.测定了所有合成化合物对5种植物病原真菌即水稻纹枯病原真菌、小麦赤霉病原真菌、玉米小斑病原真菌、油菜菌核病原真菌和番茄灰霉病原真菌的抑菌活性.初步的结果显示，大多数化合物都有显著的抑菌活性，其中，（E）-N-（4-（3-（5-溴噻吩-2-基）丙烯酰基）苯基）烟酰胺（4m）（EC₅₀=0.057 mg/L）和（E）-2-羟基-N-（4-（3-（吡啶-3-基）丙烯酰基）苯基）乙酰胺（6i）（EC₅₀=0.054 mg/L）对油菜菌核表现出最强的抑制活性，活性优于市售杀菌剂氟吡菌酰胺（EC₅₀=0.244 mg/L）.与此同时，还测定了化合物4m和6i对琥珀酸脱氢酶（SDH）的抑制活性.结果显示，它们都比氟吡菌酰胺有更好的抑制活性.分子对接研究表明，化合物4m和6i都与SDH结合得很好，结合能分别为-31.0和-31.4 kJ/mol.而且，化合物4m和6i分别与SDH的B/Trp-230残基形成了一个氢键.
关键词: 抑菌活性, 查尔酮衍生物, 分子对接, 琥珀酸脱氢酶抑制剂
Twenty nine chalcone derivatives were designed, synthesized and characterized by IR, ¹H NMR, ¹³C NMR and HRMS. The antifungal activities of all the synthesized compounds were determined against five plant pathogenic fungi namely Rhizoctonia solani, Fusarum graminearum, Helminthosporium maydis, Sclerotinia sclerotiorum and Botrytis cinerea. Preliminary results indicated that most of them revealed significant antifungal activity. Among them, (E)-N-(4-(3-(5-bromothiophen-2-yl)acryloyl)phenyl)nicotinamide (4m) (EC₅₀=0.057 mg/L) and (E)-2-hydroxy-N-(4-(3-(pyridin-3-yl)acryloyl)phenyl)ace-tamide (6i) (EC₅₀=0.054 mg/L) showed the strongest activities against S. sclerotiorum and possessed better antifungal activities than the commercial fungicide of fluopyram (EC₅₀=0.244 mg/L). Meanwhile, the inhibitory activities of compounds 4m and 6i were tested against succinate dehydrogenase (SDH). The results displayed that they had also better activities than fluopyram. Molecular docking studies demonstrated that compounds 4m and 6i bound well to SDH and their binding energies were -31.0 and -31.4 kJ/mol, respectively. Moreover, compounds 4m and 6i formed hydrogen bonds with residue B/Trp-230 of SDH, respectively.
Key words: antifungal activity, chalcone derivatives, molecular docking, succinate dehydrogenase inhibitor


PDF全文下载地址:

点我下载PDF