Song Gao-Peng, Hu De-Kun, Tian Hao, Li Ya-Sheng, Cao Yun-Shen, Jin Hong-Wei, Cui Zi-Ning
Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
Sci Rep. 2016 Mar 10;6:22977. doi: 10.1038/srep22977.
A pair of chemical isomeric structures of novel N-tert-butylphenyl thenoylhydrazide compounds I and II were designed and synthesized. Their structures were characterized by MS, IR, (1)H NMR, elemental analysis and X-ray single crystal diffraction. The regioselectivity of the Meerwein arylation reaction and the electrophilic substitution reaction of N-tert-butyl hydrazine were studied by density functional theory (DFT) quantum chemical method. The larvicidal tests revealed that some compounds I had excellent larvicidal activity against Culex pipiens pallens. As the candidates of insect growth regulators (IGRs), the larval growth inhibition and regulation against Culex pipiens pallens were examined for some compounds, especially I1 and I7. Compounds I1 and I7 were further indicated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). Finally, a molecular docking study of compound I7 was conducted, which was not only beneficial to understand the structure-activity relationship, but also useful for development of new IGRs for the control of mosquitos.
设计并合成了新型N-叔丁基苯基噻吩甲酰肼化合物I和II的一对化学异构结构。通过质谱、红外光谱、核磁共振氢谱、元素分析和X射线单晶衍射对其结构进行了表征。采用密度泛函理论（DFT）量子化学方法研究了N-叔丁基肼的Meerwein芳基化反应和亲电取代反应的区域选择性。杀幼虫试验表明，一些化合物I对淡色库蚊具有优异的杀幼虫活性。作为昆虫生长调节剂（IGRs）的候选物，对一些化合物，特别是I1和I7，进行了对淡色库蚊幼虫生长抑制和调节的研究。通过在草地贪夜蛾细胞系（Sf9细胞）上的报告基因测定，进一步表明化合物I1和I7为蜕皮甾类激动剂。最后，对化合物I7进行了分子对接研究，这不仅有助于理解构效关系，而且对开发用于控制蚊子的新型IGRs也有用。
