Notes

Synthesis and Bioactivity of Novel Pyridine Phenyl Ethers Bearing N-heterocycles

  • Dai Hong ,
  • Chen Jia ,
  • Cao Xiongfei ,
  • Miao Wenke ,
  • Shi Yujun ,
  • Fang Jianxin ,
  • Ye Linyu ,
  • Zhong Sulin
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b United Nations Nantong Pesticide Forulation Development Centre, Nantong 226006;
    c State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received date: 2015-10-19

  Revised date: 2015-11-05

  Online published: 2015-11-20

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), and the Science and Technology Project Fund of Nantong City (Nos. AS2013002, MS22015020, AS2014011).

Abstract

In order to find novel pyridine phenyl ether lead compounds, a series of novel pyridine phenyl ether derivatives containing N-heterocycles were prepared by the strategy of active substructure combination. Their structures were determined by 1H NMR, 13C NMR, IR and elemental analysis. Preliminary bioassay data displayed that some of the designed compounds exhibited good insecticidal activity. Additionally, some target compounds showed significant anti-tumor activities.

Cite this article

Dai Hong , Chen Jia , Cao Xiongfei , Miao Wenke , Shi Yujun , Fang Jianxin , Ye Linyu , Zhong Sulin . Synthesis and Bioactivity of Novel Pyridine Phenyl Ethers Bearing N-heterocycles[J]. Chinese Journal of Organic Chemistry, 2016 , 36(2) : 377 -383 . DOI: 10.6023/cjoc201510020

References

[1] Sumida, M.; Niwata, S.; Fukami, H.; Tanaka, T.; Wakabayashi, K.; Boger, P. J. Agric. Food Chem. 1995, 43, 1929.
[2] Wang, M. H.; Yang, C. L.; Jiang, M. G. World Pestic. 2002, 24, 13 (in Chinese). (王鸣华, 杨春龙, 蒋木庚, 世界农药, 2002, 24, 13.)
[3] Ning, L. H.; Peng, H.; Tu, H. Y.; He, H. W. Chin. J. Pestic. Sci. 2004, 6, 74 (in Chinese). (宁丽红, 彭浩, 涂海洋, 贺红武, 农药学学报, 2004, 6, 74.)
[4] Freundlich, J. S.; Yu, M.; Lucumi, E.; Kuo, M.; Tsai, H. C.; Valderramos, J. C.; Karagyozov, L.; Jacobs, W. R. Jr.; Schiehser, G. A.; Fidock, D. A.; Jacobus, D. P.; Sacchettini, J. C. Bioorg. Med. Chem. Lett. 2006, 16, 2163.
[5] Liu, A. P.; Feng, Q. J.; Hu, C. H.; He, H. J.; Wang, T. J.; Liu, Y.; Lei, M. X.; Pang, H. L.; He, H. W. Chin. J. Org. Chem. 2008, 28, 531 (in Chinese). (柳爱平, 冯秋菊, 胡春华, 何海军, 王婷瑾, 刘洋, 雷满香, 庞怀林, 贺红武, 有机化学, 2008, 28, 531.)
[6] Kini, S. G.; Bhat, A. R.; Byrant, B.; Williamson, J. S.; Dayan, F. E. Eur. J. Med. Chem. 2009, 44, 492.
[7] Liu, J. C.; Cui, Z. P.; He, H. W. Chin. J. Org. Chem. 2012, 32, 1925 (in Chinese). (刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1925.)
[8] Anderson, J. W.; Sarantakis, D.; Terpinski, J.; Kumar, T. R. S.; Tsai, H. C.; Kuo, M.; Ager, A. L.; Jacobs, W. R. Jr.; Schiehser, G. A.; Ekins, S.; Sacchettini, J. C.; Jacobus, D. P.; Fidock, D. A.; Freundlich, J. S. Bioorg. Med. Chem. Lett. 2013, 23, 1022.
[9] Peng, H.; Gao, Y. J.; He, H. W. Chin. J. Org. Chem. 2013, 33, 1994 (in Chinese). (彭浩, 高玉焦, 贺红武, 有机化学, 2013, 33, 1994.)
[10] Zhang, Y. P.; Tan, W.; Yang, Y. S.; Sun, S. Q.; Guo, H. C. Chin. J. Org. Chem. 2015, 35, 1985 (in Chinese). (张应鹏, 谭伟, 杨云裳, 孙世琪, 郭慧琛, 有机化学, 2015, 35, 1985.)
[11] Kleemann, A.; Baltruschat, H. S.; Huelsen, T.; Thomas, S. S. EP 0723960, 1996 [Chem. Abstr. 1996, 125, 195679].
[12] Morimoto, K.; Ohnari, M.; Furusawa, H.; Terachi, T.; Nawamaki, T.; Ishikawa, K.; Nakahira, K.; Kawaguchi, C. WO 9606096, 1996 [Chem. Abstr. 1996, 125, 58524].
[13] Xu, Y. J.; Wang, Q. H.; Wu, J. Y.; Wu, H. B.; Ran, Z. J.; Mao, C. S.; Qin, Z. H. Chin. J. Pestic. Sci. 2007, 9, 189 (in Chinese). (徐彦军, 王庆海, 武菊英, 吴厚斌, 冉兆晋, 毛朝姝, 覃兆海, 农药学学报, 2007, 9, 189.)
[14] Ran, Z. J.; Ni, H. W.; Duan, H. X.; Li, N.; Dong, Y. H.; Fu, B.; Xiao, Y. M.; Qin, Z. H. Chin. J. Pestic. Sci. 2009, 11, 41 (in Chinese). (冉兆晋, 倪汉文, 段红霞, 李楠, 董燕红, 傅滨, 肖玉梅, 覃兆海, 农药学学报, 2009, 11, 41.)
[15] Li, R. J.; Bai, Y. H.; Shi, B.; Xiao, P. F. Chin. J. Pestic. 2007, 46, 305 (in Chinese). (李瑞军, 白延海, 史犇, 肖鹏飞, 农药, 2007, 46, 305.)
[16] Li, A. J.; Liu, B. S.; Yuan, B. G. Chin. J. Pestic. 2012, 51, 416 (in Chinese). (李爱军, 刘宝擅, 苑保国, 农药, 2012, 51, 416.)
[17] Ran, Z. J.; Yuan, H. Z.; Cao, A. C.; Qin, Z. H. Chin. J. Pestic. Sci. 2010, 12, 269 (in Chinese). (冉兆晋, 袁会珠, 曹坳程, 覃兆海, 农药学学报, 2010, 12, 269.)
[18] Ran, Z. J.; Yuan, H. Z.; Cao, A. C.; Qin, Z. H. Chin. J. Pestic. Sci. 2010, 12, 458 (in Chinese). (冉兆晋, 袁会珠, 曹坳程, 覃兆海, 农药学学报, 2010, 12, 458.)
[19] Zhang, A. G.; Kayser, H.; Maienfisch, P.; Casida, J. E. J. Neurochem. 2000, 75, 1294.
[20] Zhang, G. S.; Hou, G. X. Pestic. Sci. Admin. 2004, 25, 22 (in Chinese). (张国生, 侯广新, 农药科学与管理, 2004, 25, 22.)
[21] Dai, B. J. World Pestic. 2005, 27, 46 (in Chinese). (戴宝江, 世界农药, 2005, 27, 46.)
[22] Shao, X. S.; Tian, Z. Z.; Li, Z.; Xu, X. Y.; Huang, Q. C.; Qian, X. H. Chin. J. Pestic. Sci.. 2008, 10, 117 (in Chinese). (邵旭升, 田忠贞, 李忠, 徐晓勇, 黄青春, 钱旭红, 农药学学报, 2008, 10, 117.)
[23] Yokota, T.; Mikata, K.; Nagasaki, H.; Ohta, K. J. Agric. Food Chem. 2003, 51, 7066.
[24] Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. J. Agric. Food Chem. 2007, 55, 812.
[25] Bouillot, A. M. J.; Dodic, N.; Gellibet, F. J.; Mirguet, O. WO 2009071504, 2009 [Chem. Abstr. 2009, 151, 33581].
[26] Wang, T. T.; Bing, G. F.; Zhang, X.; Qin, Z. F.; Yu, H. B.; Qin, X.; Dai, H.; Miao, W. K.; Wu, S. S.; Fang, J. X. Bioorg. Med. Chem. Lett. 2010, 20, 3348.
[27] Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484 (in Chinese). (吴珊珊, 苗文科, 王婷婷, 方建新, 有机化学, 2015, 35, 1484.)
[28] Ma, Y. M.S. Thesis, Nankai University, Tianjin, 2009 (in Chinese). (马云, 硕士论文, 南开大学, 天津, 2009.)
[29] Liu, J. C.; Liu, Y. J.; He, H. W. Chin. J. Org. Chem. 2015, 35, 462 (in Chinese). (刘建超, 刘勇军, 贺红武, 有机化学, 2015, 35, 462.)

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