5-嘧啶基-1,2,4-噁二唑衍生物的合成及生物活性研究有机化学.pdfVIP

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 6 期, 891～896 Chinese Journal of Organic Chemistry No. 6, 891～896 ·研究简报· 5-嘧啶基-1,2,4-噁二唑衍生物的合成及生物活性研究 黄统辉 涂海洋* 刘 名 侯昌健 张爱东* (华中师范大学农药与化学生物学教育部重点实验室 武汉 430079) 摘要 通过嘧啶甲酰氯与取代的苄胺肟反应得到一系列结构新颖的 5-嘧啶基-1,2,4-噁二唑类化合物, 并对其结构进行 了表征, 培养并测定了化合物 5a 的晶体结构; 将目标化合物晶体结构对接到靶酶酵母乙酰辅酶 A 羧化酶(ACCase) 的活 性位点, 发现目标化合物与复合物晶体中的禾草灵分子的构象及结合模式相似; 初步生物活性测试表明部分化合物具 有较好的除草活性. 关键词 嘧啶基-1,2,4-噁二唑; 合成; 晶体结构; 除草活性; 分子对接 Synthesis and Biological Activity of 5-Pyrimidinyl-1,2,4-oxadiazole Derivatives Huang, Tonghui Tu, Haiyang* Liu, Ming Hou, Changjian Zhang, Aidong * (Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079) Abstract A series of 5-pyrimidinyl-1,2,4-oxadiazole derivatives were synthesized by the reaction of sub- stituted benzamidoxime with pyrimidinecarbonyl chloride, and their structures were characterized. As a rep- resentative, the structure of compound 5a was confirmed with X-ray crystallography. Molecular docking was used to investigate the binding conformations of several compounds to the active site of yeast ACCase and predict the bioactivity, and the results revealed that the binding modes are similar to that as diclofop in complex with ACCase. Preliminary bioassay showed that most of title compounds have good herbicidal ac- tivity. Keywords pyrimidinyl-1,2,4-oxadiazole; synthesis; crystal structure; herbicidal activity; molecular