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.