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2016 , Vol. 36 >Issue 2: 393 - 398

DOI: https://doi.org/10.6023/cjoc201509011

研究简报

1-(吡啶-2-基)-2-芳氧基-2-(α-1H-1,2,4-三唑-1-基)乙酮的合成、晶体结构与生物活性

  • 戴红 ,
  • 刘建兵 ,
  • 陶伟峰 ,
  • 苗文科 ,
  • 方建新 ,
  • 汪清民
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  • a 南开大学元素有机化学国家重点实验室 天津 300071;
    b 南通大学化学化工学院 南通 226019

收稿日期: 2015-09-08

  修回日期: 2015-09-30

  网络出版日期: 2015-11-03

基金资助

国家自然科学基金(Nos. 20772068)、元素有机化学国家重点实验室开放课题(No. 201412)和南通市科技计划(Nos. CP12013002, AS2014011)资助项目

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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 ,
  • Liu Jianbing ,
  • Tao Weifeng ,
  • Miao Wenke ,
  • Fang Jianxin ,
  • Wang Qingmin
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  • a State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
    b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019

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)

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摘要

为了从三唑类化合物中寻找新的活性化合物, 采用活性亚结构拼接和活性叠加方法, 将吡啶环结构单元引入到三唑类化合物分子中, 制备了一系列未见文献报道的新型含吡啶环结构的三唑类衍生物. 经1H NMR, 13C NMR, IR, MS和元素分析对所合成的化合物的结构进行了表征. 此外, 采用X射线单晶衍射分析方法进一步测定了化合物4k的晶体结构. 初步的生物活性测试表明, 部分目标化合物在试验浓度下具有一定的杀菌和植物生长调节活性.

关键词： 三氮唑; 吡啶环; 合成; 生物活性

本文引用格式

戴红 , 刘建兵 , 陶伟峰 , 苗文科 , 方建新 , 汪清民 . 1-(吡啶-2-基)-2-芳氧基-2-(α-1H-1,2,4-三唑-1-基)乙酮的合成、晶体结构与生物活性[J]. 有机化学, 2016 , 36(2) : 393 -398 . DOI: 10.6023/cjoc201509011

Abstract

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

参考文献

[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

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