研究简报

新型含吡唑环结构的吡唑肟酯类化合物的合成与生物活性研究

  • 戴红 ,
  • 黄美岭 ,
  • 葛书山 ,
  • 孙思宇 ,
  • 沈爱宝 ,
  • 成晓燕 ,
  • 李春建 ,
  • 石健
展开
  • a 南通大学化学化工学院 南通 226019;
    b 南通大学药学院 南通 226001;
    c 南通大学分析测试中心 南通 226019

收稿日期: 2017-07-21

  修回日期: 2017-08-21

  网络出版日期: 2017-09-08

基金资助

国家自然科学基金(No.21372135)、江苏省“六大人才高峰”(No.2013-SWYY-013)、南通市科技计划(No.MS22015020)资助项目.

Synthesis and Biological Activities of Novel Pyrazole Oxime Esters Containing Substituted Pyrazolyl Group

  • Dai Hong ,
  • Huang Meiling ,
  • Ge Shushan ,
  • Sun Siyu ,
  • Shen Aibao ,
  • Cheng Xiaoyan ,
  • Li Chunjian ,
  • Shi Jian
Expand
  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b School of Pharmacy, Nantong University, Nantong 226001;
    c Analysis and Testing Center, Nantong University, Nantong 226019

Received date: 2017-07-21

  Revised date: 2017-08-21

  Online published: 2017-09-08

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (No. MS22015020).

摘要

为了寻找与发现具有优良生物活性的吡唑肟类衍生物,采用活性亚结构拼接方法,设计并合成了一系列未见文献报道的新型含取代吡唑环结构的吡唑肟酯类化合物.通过1H NMR,13C NMR和元素分析等方法确证了目标化合物的结构.初步的生物活性测试结果表明,在测试浓度为500 μg/mL时,部分化合物对蚜虫表现出较好的杀灭活性,部分化合物对褐飞虱显示出较好的杀灭作用.另外,部分化合物还对HepG2细胞呈现出一定的抗肿瘤活性.

本文引用格式

戴红 , 黄美岭 , 葛书山 , 孙思宇 , 沈爱宝 , 成晓燕 , 李春建 , 石健 . 新型含吡唑环结构的吡唑肟酯类化合物的合成与生物活性研究[J]. 有机化学, 2017 , 37(12) : 3289 -3295 . DOI: 10.6023/cjoc201707024

Abstract

In order to explore novel pyrazole derivatives with good biological activities, a series of pyrazole-containing pyrazole oxime esters were designed and synthesized according to the method of active substructure combination. Their structures were determined by 1H NMR, 13C NMR spectra and elemental analysis. The preliminary bioactivity test showed that some of the target compounds had good insecticidal activity against Aphis medicaginis at a concentration of 500 μg/mL, some title compounds displayed good insecticidal activity against Nilaparvata lugens at 500 μg/mL. In addition, some of the designed compounds exhibited certain anti-tumor activity against HepG2 cells.

参考文献

[1] Wang, H. Q.; Liu, H.; Liu, Z. J. Chin. J. Org. Chem. 2004, 24, 1563(in Chinese). (王宏青, 刘惠, 刘钊杰, 有机化学, 2004, 24, 1563.)
[2] Wang, H. Q.; Liu, H.; Liu, Z. J. Chin. J. Org. Chem. 2004, 24, 797(in Chinese). (王宏青, 刘惠, 刘钊杰, 有机化学, 2004, 24, 797.)
[3] Tan, C. X.; Shen, D. L.; Weng, J. Q. Ou, X. M. Chin. J. Org. Chem. 2005, 25, 1268(in Chinese). (谭成侠, 沈德隆, 翁建全, 欧晓明, 有机化学, 2005, 25, 1268.)
[4] Zhou, Z. Z.; Yang, G. F. Bioorg. Med. Chem. 2006, 14, 8666.
[5] Wu, Z. B.; Zhou, X.; Ye, Y. Q.; Wang, P. Y.; Yang, S. Chin. Chem. Lett. 2017, 28, 121.
[6] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[7] Swanson, M. B.; Ivancic, W. A.; Saxena, A. M.; Allton, J. D.; O'Brien, G. K.; Suzuki, T.; Nishizawa, H.; Nokata, M. J. Agric. Food Chem. 1995, 43, 513.
[8] Gu, B. Q.; Zhu, W. Q.; Fan, W. Z.; Qian, H.; Liu, J. M.; Zhang, A. Q.; Shen, R. X. Mod. Agrochem. 2002, 1, 9(in Chinese). (顾保权, 朱伟清, 范文政, 钱虹, 刘建梅, 张爱庆, 沈荣仙, 现代农药, 2002, 1, 9.)
[9] Fan, W. Z.; Gu, B. Q.; Zhu, W.; Zhang, Y. B. Mod. Agrochem. 2005, 4, 9(in Chinese). (范文政, 顾保权, 朱伟, 张一宾, 现代农药, 2005, 4, 9.)
[10] Lahm, G. P.; Selby T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[11] El-Tamany, E. S.; El-Shahed, F. A.; Mohamed, B. H. J. Serb. Chem. Soc. 1999, 64, 9.
[12] Wang, J. L.; Liu, D. X.; Zhang, Z. J.; Shan, S.; Han, X. B.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. W. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 7124.
[13] Zakia, M. E. A.; Solimana, H. A.; Hiekalb, Ola. A.; Rashada, A. E. Z. Naturforsch. C 2006, 61, 1.
[14] Liang, X.; Zang, J.; Zhu, M.; Gao, Q.; Wang, B.; Xu, W.; Zhang, Y. ACS Med. Chem. Lett. 2016, 7, 950.
[15] Li, J.; Huo, H.; Guo, R.; Liu, B.; Li, L.; Dan, W.; Xiao, X.; Zhang, J.; Shi, B. Eur. J. Med. Chem. 2017, 130, 1.
[16] Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160.
[17] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[18] Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest Manage. Sci. 2014, 1207.
[19] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[20] Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504.
[21] Lv, X. H.; Li, Q. S.; Ren, Z. L.; Chu, M. J.; Sun, J.; Zhang, X.; Xing, M.; Zhu, H. L.; Cao, H. Q. Eur. J. Med. Chem. 2015, 108, 586.
[22] Ouyang, G.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699.
[23] Wei, F.; Zhao, B. X.; Huang, B.; Zhang, L.; Sun, C. H.; Dong, W. L.; Shin, D. S.; Miao, J. Y. Bioorg. Med. Chem. Lett. 2006, 16, 6342.
[24] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[25] Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[26] Shi, Y. J.; Li, Y.; Fang, Y.; Ye, L. Y.; Chen, J.; Dai, H. Chin. J. Org. Chem. 2016, 36, 1431(in Chinese). (石玉军, 李阳, 方源, 叶林玉, 陈佳, 戴红, 有机化学, 2016, 36, 1431.)

文章导航

/