Citation: Dai Hong, Liu Jianbing, Tao Weifeng, Miao Wenke, Fang Jianxin, Wang Qingmin. Synthesis, Crystal Structure and Biological Activity of Novel 1-(Pyridin-2-yl)-2-aryloxy-2-(1H-1,2,4-triazol-1-yl)ethanones[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 393-398. doi: 10.6023/cjoc201509011 shu

Synthesis, Crystal Structure and Biological Activity of Novel 1-(Pyridin-2-yl)-2-aryloxy-2-(1H-1,2,4-triazol-1-yl)ethanones

Dai Hong ^a,b,, ,
Liu Jianbing ^a ,
Tao Weifeng ^a ,
Miao Wenke ^a ,
Fang Jianxin ^a,, ,
Wang Qingmin ^a

1.
a State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
2.
b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019

Corresponding author: Dai Hong, Fang Jianxin,
Received Date: 8 September 2015
Available Online: 30 September 2015
Fund Project: 国家自然科学基金(Nos. 20772068) (Nos. 20772068)元素有机化学国家重点实验室开放课题(No. 201412) (No. 201412)南通市科技计划(Nos. CP12013002, AS2014011)资助项目 (Nos. CP12013002, AS2014011)

In order to find novel triazole lead compounds, a series of new triazole derivatives containing pyridine moiety were synthesized by the introduction of the important pyridyl backbone into the molecules of triazoles. They were structurally confirmed by ¹H NMR, ¹³C NMR, IR, MS and elemental analysis. Additionally, compound 4k was structurally characterized through X-ray single crystal diffraction method. Preliminary bioassay data showed that some of the title compounds displayed moderate fungicidal and plant growth regulatory activities.
- triazole,
- pyridine,
- synthesis,
- bioactivity
1. [1]
  [1] Jin, Z.; Liu, W.; Hu, Y.; Liu, J. B.; Shao, L.; Fang, J. X. Chin. J. Org. Chem. 2005, 25, 972 (in Chinese). (金钟, 刘伟, 胡燕, 刘建兵, 邵玲, 方建新, 有机化学, 2005, 25, 972.)
2. [2]
  [2] Liu, J. B.; Li, L. C.; Dai, H,; Liu, Z.; Fang, J. X. J. Organomet. Chem. 2006, 691, 2686.
3. [3]
  [3] Yu, H. B.; Shao, L.; Fang, J. X. J. Organomet. Chem. 2007, 692, 991.
4. [4]
  [4] Isloor, A. M.; Kalluraya, B.; Shetty, P. Eur. J. Med. Chem. 2009, 44, 3784.
5. [5]
  [5] Xu, W. M.; Song, B. A.; Yang, S.; Hu, D. Y.; Zeng, S. Chin. J. Pestic. 2010, 49, 625 (in Chinese). (徐维明, 宋宝安, 杨松, 胡德禹, 曾松, 农药, 2010, 49, 625.)
6. [6]
  [6] Bao, X. P.; Lin, X. F.; Jian, J. Y.; Zhang, F.; Zou, L. B. Chin. J. Org. Chem. 2013, 33, 995 (in Chinese). (鲍小平, 林选福, 蹇军友, 张峰, 邹林波, 有机化学, 2013, 33, 995.)
7. [7]
  [7] Wang, M. M.; Duan, Y. C.; Ye, X. W.; Ren, J. L.; Yu, B.; Zhang, E.; Liu, H. M. Chin. J. Org. Chem. 2013, 33, 2384 (in Chinese). (王盟盟, 段迎超, 叶先炜, 任景丽, 余斌, 张恩, 刘宏民, 有机化学, 2013, 33, 2384.)
8. [8]
  [8] Wang, H. L.; Ruan, L. L.; Chen, Y.; Liu, X. H.; Weng, J. Q. Chin. J. Org. Chem. 2014, 34, 419 (in Chinese). (王海林, 阮铃莉, 陈勇, 刘幸海, 翁建全, 有机化学, 2014, 34, 419.)
9. [9]
  [9] Han, J.; Zhou, X. X.; Chen, S. B.; An, Y. Chin. J. Org. Chem. 2014, 34, 741 (in Chinese). (韩杰, 周晓霞, 陈思宝, 安悦, 有机化学, 2014, 34, 741.)
10. [10]
  [10] Li, Y. C.; Cheng, J. R.; Zheng, J. Y. Chin. J. Pestic. 1993, 32, 11 (in Chinese). (李煜昶, 成俊然, 郑健禺, 农药, 1993, 32, 11.)
11. [11]
  [11] Li, Y. C. Chin. J. Pestic. 1993, 32, 20 (in Chinese). (李煜昶, 农药, 1993, 32, 20.)
12. [12]
  [12] Goa, K. L.; Barradell, L. B. Drugs 1996, 51, 585.
13. [13]
  [13] Haria, M.; Bryson, H. M.; Goa, K. L. Drugs 1996, 50, 658.
14. [14]
  [14] Casali, A.; Sega, F. M.; Casali, M.; Giuntini, T.; Cappellini, G. C.; Terzoli, E. J. Exp. Clin. Cancer Res. 2000, 19, 17.
15. [15]
  [15] Jo, Y. W.; Im, W. B.; Rhee, J. K.; Shim, M. J..; Kim, W. B.; Choi, E. C. Bioorg. Med. Chem. 2004, 12, 5909.
16. [16]
  [16] Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288.
17. [17]
  [17] Singh, P.; Kaur, P.; Luxami, V.; Kaur, S.; Kumar, S. Bioorg. Med. Chem. 2007, 15, 2386.
18. [18]
  [18] Xiao, L. X.; Shi, D. Q. Chin. J. Org. Chem. 2010, 30, 85 (in Chinese). (肖琳霞, 石德清, 有机化学, 2010, 30, 85.)
19. [19]
  [19] Liu, J.; Xie, H. P.; Song, B. A.; Hu, D. Y.; Yang, S.; Jin, L. H.; Xue, W.; Wu, J,; Xu, W. M. Chin. J. Org. Chem. 2010, 30, 1347 (in Chinese). (刘杰, 谢化鹏, 宋宝安, 胡德禹, 杨松, 杨松, 金林红, 薛伟, 吴剑, 徐维明, Chin. J. Org. Chem. 2010, 30, 1347.)
20. [20]
  [20] Dai, H.; Shi, L.; Zhang, H. J.; Li, Y. Q.; Fang, J. X.; Shi, Y. J. Chin. J. Org. Chem. 2012, 32, 1060 (in Chinese). (戴红, 施磊, 张海军, 李永强, 方建新, 石玉军, 有机化学, 2012, 32, 1060.)
21. [21]
  [21] Xiong, Z.; Li, H. C.; Liang, N.; Yin, J.; Lu, P.; Xue, W. Chin. J. Org. Chem. 2012, 32, 1473 (in Chinese). (熊壮, 李海畅, 梁娜, 尹娟, 卢平, 薛伟, 有机化学, 2012, 32, 1473.)
22. [22]
  [22] Yamamoto, I.; Tomizawa, M.; Saito, T.; Miyamoto, T.; Walcott, E. C.; Sumikawa, K. Arch. Insect Biochem. Physiol. 1998, 37, 24.
23. [23]
  [23] Kiriyama, K.; Itazu, Y.; Kagabu, S. J. Pest. Sci. 2003, 28, 8.
24. [24]
  [24] Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. J. Agric. Food Chem. 2007, 55, 812.
25. [25]
  [25] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 秦雪, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1662.)
26. [26]
  [26] Harvey, W. J. J. Org. Chem. 1959, 24, 872.
27. [27]
  [27] Liu, J. B.; Tao, W. F.; Hu, Y.; Dai, H.; Fang, J. X. Chin. J. Org. Chem. 2006, 26, 1566 (in Chinese). (刘建兵, 陶伟峰, 胡燕, 戴红, 方建新, 有机化学, 2006, 26, 1566.)
28. [28]
  [28] Liu, J. B.; Tao, W. F.; Dai, H.; Jin, Z.; Fang, J. X. Heteroat. Chem. 2007, 18, 376.
29. [29]
  [29] Jin, Z.; Hu, Y.; Huo, A. H.; Tao, W. F.; Shao, L.; Liu, J. B.; Fang, J. X. J. Organomet. Chem. 2006, 691, 2340.
30. [30]
  [30] Zhang, M.; Luo, X. A.; Zhu, D. Z.; Zhang, X. P.; Liu, F.; Fang, J. X.; Liu, J. B. Chin. J. Org. Chem. 2013, 33, 1955 (in Chinese). (张沐, 罗喜爱, 祝岱帧, 张雪鹏, 刘凤, 方建新, 刘建兵, 有机化学, 2013, 33, 1955.)
31. [31]
  [31] Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
10. [10]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
11. [11]
  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
12. [12]
  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
13. [13]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
14. [14]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
15. [15]
  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
16. [16]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
17. [17]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
18. [18]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
19. [19]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
20. [20]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(738)
HTML views(69)

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