新型含偕二甲基环丙烷的4-甲基-1,2,4-三唑硫醚化合物的合成、生物活性及三维定量构效关系(3D-QSAR)研究  

Synthesis,Biological Activity and Three-Dimensional Quantitative Structure-Activity Relationship(3D-QSAR)Study of Novel 4-Methyl-1,2,4-triazole-thioethers Containing gem-Dimethylcyclopropane Ring

作　　者：虞友培 段文贵[1] 林桂汕[1] 康国强 王晓宇 雷福厚 Yu Youpei;Duan Wengui;Lin Guishan;Kang Guoqiang;Wang Xiaoyu;Lei Fuhou(College of Chemistry and Chemical Engineering,Guangxi University,Nanning 530004;Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi University for Nationalities,Nanning 530008)

机构地区：[1]广西大学化学化工学院,南宁530004 [2]广西民族大学广西林产化学与工程重点实验室,南宁530008

出　　处：《有机化学》2020年第6期1647-1657,共11页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.31870556);广西科技基地和人才专项(No.AD18126005)资助项目.

摘　　要：为了探寻有效的新型生物活性分子,通过多步反应设计并合成了一系列新型含偕二甲基环丙烷的4-甲基-1,2,4-三唑硫醚衍生物,通过UV-Vis,FTIR,NMR,ESI-MS和元素分析等方法对所有目标化合物的结构进行了表征.初步测定了目标化合物的抑菌和除草活性.生物活性结果显示,在质量浓度为50μg/mL时,有2个化合物对苹果轮纹病菌表现出明显的抑菌活性,优于阳性对照百菌清.此外,在质量浓度为100μg/mL时,有4个化合物对油菜胚根生长表现出优异的抑制活性,优于阳性对照丙炔氟草胺.为了开发出更有效的抗苹果轮纹病菌化合物,使用比较分子力场分析(CoMFA)方法对目标化合物的抗苹果轮纹病菌活性进行了初步的三维定量构效关系(3D-QSAR)分析,建立了一个合理有效的3D-QSAR模型(r^2=0.985, q^2=0.509).A series of novel 4-methyl-1,2,4-triazole-thioethers containing gem-dimethylcyclopropane ring were designed and synthesized by multi-step reactions in search of potent novel bioactive molecules.Structures of all the target compounds were characterized by means of UV-Vis,FTIR,NMR,ESI-MS,and elemental analysis.The antifungal and herbicidal activities of the target compounds were preliminarily evaluated.As indicated in bioassay results,2 compounds exhibited excellent antifungal activity against Physalospora piricola,which are much better than that of the commercial fungicide of chlorothalonil used as positive control.Also,at 100µg/mL,4 compounds displayed prominent herbicidal activity against the root-growth of rape(Brassica campestris),which are much better than that of the commercial herbicide of flumioxazin used as positive control.In the interest of developing more effective antifungal compounds against P.piricola,the preliminary analysis of three-dimensional quantitative structure-activity relationship(3D-QSAR)was carried out using the molecular field analysis(CoMFA)method,and a reasonable and effective 3D-QSAR model(r^2=0.985,q^2=0.509)has been established.

关 键 词：偕二甲基环丙烷 3-蒈烯 1 2 4-三唑硫醚 生物活性 三维定量构效关系(3D-QSAR) 

分 类 号：O621.3[理学—有机化学]