新型蒎烷基吡唑酰胺类衍生物的合成及其生物活性研究  

Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives

作　　者：芮坚 张齐[1] 王欣[2] 徐徐[1,3,4] 徐海军[1] 饶卫东[1] 王石发[1,3,4] 

机构地区：[1]南京林业大学化学工程学院,南京210037 [2]南京农业大学植物保护学院,南京210095 [3]江苏省生物质绿色燃料与化学品重点实验室,南京210037 [4]广西林产化学与工程重点实验室,南宁530008

出　　处：《有机化学》2017年第1期218-225,共8页Chinese Journal of Organic Chemistry

基　　金：江苏省高校自然科学研究重大项目(No.14KJ220001);国家自然科学基金(No.31470529);广西林产化学与工程重点实验室开放基金(No.JSBEM2014010)资助项目~~

摘　　要：以诺蒎酮为原料,合成了新型蒎烷基吡唑酰胺类衍生物,并对其生物活性进行了研究.诺蒎酮与芳香醛进行缩合反应,得到中间体3-芳亚甲基诺蒎酮2a^2g,2a^2g与水合肼经环化、脱氢芳构化反应,得到新型蒎烷基吡唑类化合物3a^3g;以N,N-二甲基甲酰胺为溶剂,3a^3g与2-氯乙酰胺在碱催化作用下,合成了7种吡唑酰胺类化合物4a^4g.其结构经~1H NMR,^(13)C NMR,IR,和HRMS表征.通过X射线衍射分析测定了化合物2-(6',6'-二甲基-3'-(4'-甲氧基苯基)-4',5',6',7'-四氢-5',7'-桥亚甲基-吲唑-1'-基)乙酰胺(4d)的晶体结构.探讨了化合物3a^3g和4a^4g的抑菌活性和对蚜虫的杀虫活性.实验结果表明,2-(6',6'-二甲基-3'-(4'-氟苯基)-4',5',6',7'-四氢-5',7'-桥亚甲基-吲唑-1'-基)乙酰胺(4g)既具有较好的抑菌效果,同时对紫薇蚜虫也表现出较好的杀虫活性.Novel pinanyl pyrazole derivatives were synthesized from nopinone and their bioactivities were also examined in this paper. The intermediate compounds 3-arylidenenopinones 2a～2g were synthesized by condensation of aromatic aldehydes and nopinone, and pinanyl pyrazole derivatives 3a～3g were subsequently obtained by cyclization and dehydroaromatization of compounds 2a～2g and hydrazine hydrate in the circumstance of N,N-dimethylformamide（DMT）. The target compound pinanyl pyrazole acetamide derivatives 4a～4g were synthesized by alkylation using 2-chloroacetamide as the alkylating agent under the condition of base catalysis. The structures of synthesized compounds were characterized by ～1H NMR, ～（13）C NMR, IR, HRMS, and X-ray diffraction analysis. Biological activities evaluation of compounds 3a～3g and 4a～4g were performed including antibacterial and insecticidal activities on Tinocallis kahawaluokalani. Test results showed that compound 4g was a more potent bactericide and fungicide than others because of its good activities against bacteria and fungi; furthermore, compound 4g had shown the better insecticidal activity against Tinocallis kahawaluokalani than the others.

关 键 词：诺蒎酮 蒎烷基吡唑衍生物 抑菌活性 杀虫活性 

分 类 号：O626.21[理学—有机化学]