有机化学 ›› 2019, Vol. 39 ›› Issue (7): 2053-2061.DOI: 10.6023/cjoc201902027 上一篇    下一篇

研究简报

新型含1,2,4-三唑环结构的吡唑肟醚化合物的合成及其生物活性

王誉蓉a, 郑丹丹b, 王杨b, 叶浩b, 姚炜b, 丁颖b, 顾海鹰a, 冯霞b, 李玲b, 戴红b,c   

  1. a 南通大学公共卫生学院 南通 226019;
    b 南通大学化学化工学院 南通 226019;
    c 南通丰田化工有限公司 南通 226005
  • 收稿日期:2019-02-25 修回日期:2019-03-22 出版日期:2019-07-25 发布日期:2019-04-08
  • 通讯作者: 顾海鹰, 戴红 E-mail:guhy99@21cn.com;daihong_2015@aliyun.com
  • 基金资助:

    国家自然科学基金(Nos.21874077,21475070,21372135)和南通市科技计划(No.MS12017022-4)资助项目.

Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing 1,2,4-Triazole Moiety

Wang Yuronga, Zheng Dandanb, Wang Yangb, Ye Haob, Yao Weib, Ding Yingb, Gu Haiyinga, Feng Xiab, Li Lingb, Dai Hongb,c   

  1. a School of Public Health, Nantong University, Nantong 226019;
    b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    c Nantong Fengtian Chemical Industry Co. Ltd, Nantong 226005
  • Received:2019-02-25 Revised:2019-03-22 Online:2019-07-25 Published:2019-04-08
  • Contact: 10.6023/cjoc201902027 E-mail:guhy99@21cn.com;daihong_2015@aliyun.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21874077, 21475070, 21372135), and the Science and Technology Project Fund of Nantong City (No. MS12017022-4).

利用活性亚结构拼接原理,设计制备了18个未见文献报道的新型含1,2,4-三唑环结构单元的吡唑肟醚衍生物.通过1H NMR、13C NMR和元素分析等手段确认了其结构.初步的生物活性测试结果表明,部分目标化合物对粘虫、蚜虫和朱砂叶螨表现出良好的杀灭效果.在测试浓度为500 μg/mL时,目标化合物对粘虫的致死率在90%~100%,与对照药阿维菌素的杀虫效果相近,其中有4个化合物对蚜虫的致死率均为100%,与对照药吡虫啉的防效相当;1-甲基-3-甲基-5-(3,5-二氟苯氧基)-1H-吡唑-4-甲醛-O-[4-(1H-1,2,4-三唑-1-基)苯甲基]肟(8p)对朱砂叶螨的致死率为100%,与对照药唑螨酯的防效相当.当测试浓度降为100 μg/mL时,5个化合物对粘虫的致死率在90%~100%,3个化合物对蚜虫的致死率在80%~100%;化合物8p对朱砂叶螨的致死率为80%.当测试浓度降至20 μg/mL时,2个化合物对粘虫的致死率分别为75%和70%.另外,部分化合物对人肝癌(SMMC-7721)细胞显示出一定的抗肿瘤活性.

关键词: 1,2,4-三唑, 吡唑肟醚, 合成, 生物活性

Eighteen novel pyrazole oxime ethers containing 1,2,4-triazole moiety were designed and synthesized according to the method of active substructure combination. Their structures were characterized by 1H NMR, 13C NMR, and elemental analyses. Preliminary bioassay showed that some target compounds showed good insecticidal activities against Oriental armyworm, Aphis medicaginis and Tetranychus cinnabarinus. At the concentration of 500 μg/mL, target compounds had insecticidal activity against Oriental armyworm with 90%~100%, which were similar to the control of avermectin, four compounds showed 100% insecticidal activity against Aphis medicaginis, which were similar to imidacloprid. The lethal rate of 1- methyl-3-methyl-5-(3,5-difluorophenoxy)-1H-pyrazole-4-carbaldehyde-O-[4-(1H-1,2,4-triazol-1-yl)phenylmethyl]oxime (8p) against Tetranychus cinnabarinus was 100%, which was similar to that of fenpyroximate. When the concentration was reduced to 100 μg/mL, six compounds exhibited insecticidal activity against Oriental armyworm with 90%~100%, three compounds showed insecticidal activity against Aphis medicaginis with 80%~100%, and compound 8p had acaricidal activity against Tetranychus cinnabarinus with 80%. At the concentration of 20 μg/mL, the lethal rates of two compounds against Oriental armyworm were 75% and 70%, respectively. Additionally, some compounds exhibited certain anti-tumor activity against human hepatocellular carcinoma SMMC-7721 cells.

Key words: 1,2,4-triazole, pyrazole oxime ether, synthesis, bioactivity