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

doi:10.6023/cjoc201510020

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 377-383.DOI: 10.6023/cjoc201510020 Previous Articles Next Articles

Notes

新型含氮杂环结构的吡啶苯醚类化合物的合成与生物活性研究

戴红^a,c, 陈佳^a, 曹雄飞^b, 苗文科^c, 石玉军^a,b, 方建新^c, 叶林玉^a, 仲苏林^b

a 南通大学化学化工学院南通 226019;
b 联合国南通农药剂型开发中心南通 226006;
c 南开大学元素有机化学国家重点实验室天津 300071

收稿日期:2015-10-19 修回日期:2015-11-05 发布日期:2015-11-20
通讯作者: 石玉军, 仲苏林 E-mail:yjshi2015@163.com;zhongslnt@163.com
基金资助:
国家自然科学基金(Nos. 21202089, 21372135)和南通市科技计划(Nos. AS2013004, MS22015020, AS2014011)资助项目

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

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:2015-10-19 Revised:2015-11-05 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).

1. Synthesis and Bioactivity of Novel Pyridine Phenyl Ethers Bearing N-heterocycles.PDF(824KB)

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.

Key words: N-heterocycle, pyridine phenyl ether, synthesis, bioactivity

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]. Chin. J. Org. Chem., 2016, 36(2): 377-383.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.)

新型含氮杂环结构的吡啶苯醚类化合物的合成与生物活性研究

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

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.