Citation: 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 shu

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

Dai Hong ^a,c ,
Chen Jia ^a ,
Cao Xiongfei ^b ,
Miao Wenke ^c ,
Shi Yujun ^a,b,, ,
Fang Jianxin ^c ,
Ye Linyu ^a ,
Zhong Sulin ^b,,

1.
a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
2.
b United Nations Nantong Pesticide Forulation Development Centre, Nantong 226006;
3.
c State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Corresponding author: Shi Yujun, Zhong Sulin,
Received Date: 19 October 2015
Available Online: 5 November 2015
Fund Project: 国家自然科学基金(Nos. 21202089, 21372135) (Nos. 21202089, 21372135)南通市科技计划(Nos. AS2013004, MS22015020, AS2014011)资助项目 (Nos. AS2013004, MS22015020, AS2014011)

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.
- N-heterocycle,
- pyridine phenyl ether,
- synthesis,
- bioactivity
1. [1]
  [1] Sumida, M.; Niwata, S.; Fukami, H.; Tanaka, T.; Wakabayashi, K.; Boger, P. J. Agric. Food Chem. 1995, 43, 1929.
2. [2]
  [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. [3]
  [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. [4]
  [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. [5]
  [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. [6]
  [6] Kini, S. G.; Bhat, A. R.; Byrant, B.; Williamson, J. S.; Dayan, F. E. Eur. J. Med. Chem. 2009, 44, 492.
7. [7]
  [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. [8]
  [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. [9]
  [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. [10]
  [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. [11]
  [11] Kleemann, A.; Baltruschat, H. S.; Huelsen, T.; Thomas, S. S. EP 0723960, 1996 [Chem. Abstr. 1996, 125, 195679].
12. [12]
  [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. [13]
  [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. [14]
  [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. [15]
  [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. [16]
  [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. [17]
  [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. [18]
  [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. [19]
  [19] Zhang, A. G.; Kayser, H.; Maienfisch, P.; Casida, J. E. J. Neurochem. 2000, 75, 1294.
20. [20]
  [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. [21]
  [21] Dai, B. J. World Pestic. 2005, 27, 46 (in Chinese). (戴宝江, 世界农药, 2005, 27, 46.)
22. [22]
  [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. [23]
  [23] Yokota, T.; Mikata, K.; Nagasaki, H.; Ohta, K. J. Agric. Food Chem. 2003, 51, 7066.
24. [24]
  [24] Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. J. Agric. Food Chem. 2007, 55, 812.
25. [25]
  [25] Bouillot, A. M. J.; Dodic, N.; Gellibet, F. J.; Mirguet, O. WO 2009071504, 2009 [Chem. Abstr. 2009, 151, 33581].
26. [26]
  [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. [27]
  [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. [28]
  [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. [29]
  [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.)
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
3. [3]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
4. [4]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
5. [5]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
6. [6]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
7. [7]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
8. [8]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
9. [9]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
10. [10]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
11. [11]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
12. [12]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
13. [13]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
14. [14]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
15. [15]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
16. [16]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
17. [17]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
18. [18]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
19. [19]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
20. [20]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1003)
HTML views(90)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142