2-硝基-1-芳乙烯类化合物的设计合成及其对稻瘟病菌的抑制活性  

Design, synthesis and inhibitory activity of 2-nitro-1-arylethylene derivatives against Magnaporthe grisea

作　　者：覃念[1] 陈海峰[2] 任彦亮[3] 

机构地区：[1]重庆三峡学院环境与化学工程学院,重庆404100 [2]钦州学院海洋学院,广西钦州535011 [3]华中师范大学化学学院,农药与化学生物学教育部重点实验室,武汉430079

出　　处：《农药学学报》2016年第6期697-702,共6页Chinese Journal of Pesticide Science

摘　　要：为了筛选得到对稻瘟病菌Magnaporthe grisea具有较高抑菌活性的新型化合物,根据稻瘟病菌中1,3,8-三羟基萘还原酶(3HNR)的结构信息,设计合成了系列2-硝基-1-芳乙烯(2a^2e)和2-溴-2-硝基-1-芳乙烯(3a,3b)目标化合物,并测试了其对3HNR和稻瘟病菌的抑制活性,同时运用分子对接方法对目标化合物与3HNR可能的结合模式进行了分析。结果表明:大部分目标化合物对3HNR都有很好的抑制作用(IC50<5.0μmol/L),其中,化合物3的抑制活性最好,IC_(50)值为0.53μmol/L。在50μg/m L下,目标化合物对稻瘟病菌的生长具有不同程度的抑制作用,其中2e、3a和3b的抑制率高于96%;3a和3b的EC_(50)值分别为16.4和11.6μg/m L。分子对接方法分析结果表明,硝基苯乙烯骨架结构与稻瘟病菌的3HNR活性空腔的氨基酸残基有较好的相互作用,其中化合物3中的溴原子可与3HNR中Tyr223和Tyr178的羟基形成氢键,从而解释了化合物3对3HNR有较好抑制作用的原因。In order to screen novel inhibitors against Magnaporthe grisea, substituted 2-nitro-1-arylethylene（2） and substituted 2-bromo-2-nitro-1-arylethylene derivatives（3） were rationally designed and synthesized based on the structural information of 1,3,8-trihydroxynaphthalene reductase（3HNR）.In addition, Inhibition assay for 3HNR and antifungal activity to M. grisea are done,furthermore, the probable binding mode of 3HNR and target compound was analyzed by using Molecular Docking method. Results showed that most of target compounds possessed high inhibitoryactivity against 3HNR（IC50 5.0 μmol/L）. In comparison, compounds 3a and 3b showed the highest inhibitory activity（IC50 = 0.53 μmol/L）. Most of the compounds exhibited certain antifungal activity to M. grisea at 50 μg/m L, the inhibition rate of 2e, 3a and 3b exceeded 96%. Compound 3a and 3b exhibited excellent antifungal activity against M. grisea（EC50 = 16.4 μg/m L for 3a, EC50 = 11.6 μg/m L for 3b, respectively）. Analysis result of Molecular Docking method indicated that nitrostyrene compounds showed strong interactions with 3HNR from M. grisea. The hydrogen bonds between the Br atoms of the compound 3 and two hydroxyl groups, separately from Tyr223 and Tyr178 of 3HNR explain the excellent inhibitory activity of compound 3.

关 键 词：2-硝基-1-芳乙烯 稻瘟病菌 1 3 8-三羟基萘酚还原酶(3HNR) 抑菌活性 分子对接 

分 类 号：S481.8[农业科学—农药学]