文献类型：期刊文献

中文题名：吡唑并嘧啶衍生物的设计、合成、杀虫活性及其与γ -氨基丁酸受体的结合模式

英文题名：Design, synthesis, insecticidal activities and binding mode withγ-aminobutyric acid receptor of pyrazolopyrimidine derivatives

作者：栗广龙[1];江卓媛[1];周聪[1];须志平[1];李忠[1];程家高[1]

机构：[1]华东理工大学药学院,上海市化学生物学(芳香杂环)重点实验室,上海200237

年份：2021

卷号：23

期号：5

起止页码：845

中文期刊名：农药学学报

外文期刊名：Chinese Journal of Pesticide Science

收录：CSTPCD;;北大核心:【北大核心2020】；CSCD:【CSCD2021_2022】；

基金：国家自然科学基金(21572059).

语种：中文

中文关键词：吡唑并嘧啶;氟虫腈;骨架跃迁;杀虫活性;γ-氨基丁酸受体;结合模式

外文关键词：pyrazolopyrimidine;fipronil;scaffold hopping;insecticidal activities;γ-aminobutyric acid receptor;binding mode

摘要：基于氟虫腈低能构象进行骨架跃迁,设计、合成了25个未见文献报道的苯基吡唑并嘧啶胺和苯基吡唑并嘧啶酮类化合物,所有化合物的结构均通过核磁共振氢谱(^(1)H NMR)、碳谱(^(13)C NMR)及高分辨质谱(HRMS)确证。杀虫活性测试表明,目标化合物A5、B1、B4和B5在500 mg/L下对小菜蛾的致死率在40%~73%之间,活性弱于氟虫腈。初步分析,其理化性质以及其与昆虫γ-氨基丁酸(GABA)受体结合模式方面的差异可能是导致这些化合物活性比氟虫腈低的主要原因。
Twenty-five novel phenylpyrazole-pyrimidinamine and phenylpyrazole-pyrimidinone compounds were designed and synthesized based on the low-energy conformation of fipronil using scaffold hopping strategy.Their structures were confirmed by ^(1)H NMR,^(13)C NMR and HRMS.The insecticidal activity study indicated that compounds A5,B1,B4 and B5 showed 40%-73%mortality to Plutella xylostella at 500 mg/L.However,the insecticidal activities were still weaker than that of fipronil.The differences in physicochemical properties and binding mode with insectivalγ-aminobutyric acid(GABA)receptor between these compounds and fipronil may be the major factor which reduced the insecticidal activities.