Chinese Journal of Organic Chemistry >
Synthesis, Crystal Structure and Biological Activity of Novel 1-(Pyridin-2-yl)-2-aryloxy-2-(1H-1,2,4-triazol-1-yl)ethanones
Received date: 2015-09-08
Revised date: 2015-09-30
Online published: 2015-11-03
Supported by
Project supported by the National Natural Science Foundation of China (No. 20772068), the Open Project Fund of State Key Laboratory of Elemento-organic Chemistry (No. 201412), and the Science and Technology Project Fund of Nantong City (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.
Key words: triazole; pyridine; synthesis; bioactivity
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
[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] Liu, J. B.; Li, L. C.; Dai, H,; Liu, Z.; Fang, J. X. J. Organomet. Chem. 2006, 691, 2686.
[3] Yu, H. B.; Shao, L.; Fang, J. X. J. Organomet. Chem. 2007, 692, 991.
[4] Isloor, A. M.; Kalluraya, B.; Shetty, P. Eur. J. Med. Chem. 2009, 44, 3784.
[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] 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] 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] 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] 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] 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] Li, Y. C. Chin. J. Pestic. 1993, 32, 20 (in Chinese). (李煜昶, 农药, 1993, 32, 20.)
[12] Goa, K. L.; Barradell, L. B. Drugs 1996, 51, 585.
[13] Haria, M.; Bryson, H. M.; Goa, K. L. Drugs 1996, 50, 658.
[14] Casali, A.; Sega, F. M.; Casali, M.; Giuntini, T.; Cappellini, G. C.; Terzoli, E. J. Exp. Clin. Cancer Res. 2000, 19, 17.
[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] Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288.
[17] Singh, P.; Kaur, P.; Luxami, V.; Kaur, S.; Kumar, S. Bioorg. Med. Chem. 2007, 15, 2386.
[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] 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] 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] 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] Yamamoto, I.; Tomizawa, M.; Saito, T.; Miyamoto, T.; Walcott, E. C.; Sumikawa, K. Arch. Insect Biochem. Physiol. 1998, 37, 24.
[23] Kiriyama, K.; Itazu, Y.; Kagabu, S. J. Pest. Sci. 2003, 28, 8.
[24] Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. J. Agric. Food Chem. 2007, 55, 812.
[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] Harvey, W. J. J. Org. Chem. 1959, 24, 872.
[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] Liu, J. B.; Tao, W. F.; Dai, H.; Jin, Z.; Fang, J. X. Heteroat. Chem. 2007, 18, 376.
[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] 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] Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467
/
〈 |
|
〉 |