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2013 , Vol. 33 >Issue 05: 1005 - 1009

DOI: https://doi.org/10.6023/cjoc201212025

研究论文

1-(3-吲哚基)-3-芳基-2-丙烯-1-酮肟醚的合成及抑菌活性

  • 王美岩 ,
  • 曲智强 ,
  • 杜丹 ,
  • 姜林
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  • 山东农业大学化学与材料科学学院 泰安 271018

收稿日期: 2012-12-16

  修回日期: 2013-01-20

  网络出版日期: 2013-01-23

基金资助

山东省自然科学基金(No. ZR2009BM044)资助项目.

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Synthesis and Antifungal Activity of Novel 1-(3-Indoly)-3-aryl-2-propen-1-one Oxime Ethers

  • Wang Meiyan ,
  • Qu Zhiqiang ,
  • Du Dan ,
  • Jiang Lin
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  • College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018

Received date: 2012-12-16

  Revised date: 2013-01-20

  Online published: 2013-01-23

Supported by

Project supported by the Natural Science Foundation of Shandong Province (No. ZR2009BM044).

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摘要

为寻找具有优良杀菌活性的吲哚衍生物, 以吲哚等为原料利用Vilsmeier反应制得3-乙酰吲哚, 然后经过羟醛缩合、加成-消除反应合成了一系列新型含吲哚环的2-丙烯-1-酮肟醚3a～3j, 其结构通过IR, 1H NMR, ESI-MS和元素分析确证. 用生长速率法测试了目标化合物对番茄灰霉菌和西瓜炭疽菌的离体抑菌活性, 结果表明化合物对两种病原菌有一定的抑制活性, 其中3f和3g对番茄灰霉菌抑制活性较高, 在浓度为100 μg/mL时抑制率分别为81%和74%.

关键词： 吲哚; 丙烯酮; 肟醚; 合成; 抑菌活性

本文引用格式

王美岩 , 曲智强 , 杜丹 , 姜林 . 1-(3-吲哚基)-3-芳基-2-丙烯-1-酮肟醚的合成及抑菌活性[J]. 有机化学, 2013 , 33(05) : 1005 -1009 . DOI: 10.6023/cjoc201212025

Abstract

With the aim of finding novel indole derivatives with high antifungal activity, 3-acetyl indole was prepared using indole and other chemicals as starting materials through the Vilsmeier reaction, followed by reactions of aldol condensation and addition-elimination to synthesize a series of novel 2-propen-1-one oxime ethers containing indole moiety 3a～3j, and their structures were elucidated by IR, 1H NMR, MS techniques and elemental analysis. The target compounds were tested for in-vitro antifungal activities against Botrytis cinerea and Anthracnose pathogen by the mycelium growth rate method, and the result indicated that 3f and 3g displayed good antifungal activity against Botrytis cinerea at a concentration of 100 μg/mL, with inhibition rates of 81% and 74%, respectively.

Key words： indole; propenone; oxime ether; synthesis; antifungal activity

参考文献

[1] Li, J. T.; Dai, H. G.; Lin, Z. P. Prog. Chem. 2007, 19, 751 (in Chinese).
(李记太, 代红光, 蔺志平, 化学进展, 2007, 19, 751.)
[2] Hayashi, S.; Ueno, N.; Murase, A.; Nakagawa, Y.; Takada, J. Eur. J. Med. Chem. 2012, 50, 179.
[3] Golob, T.; Liebl, R.; Von Angerer, E. Bioorg. Med. Chem. 2002, 10, 3941.
[4] El-Nakkady, S, S.; Hanna, M. M.; Roaiah, H. M. Ghannam, I. A. Y. Eur. J. Med. Chem. 2012, 47, 387.
[5] Acton III, J. J.; Black, R. M.; Jones, A. B.; Moller, D. E.; Colwell, L.; Doebber, T. W.; MacNaul, K. L.; Bergerb, J.; Wood, H. B. Bioorg. Med. Chem. Lett. 2005, 15, 357.
[6] Ye, Y.; Zhao, Z. G.; Liu, X. L.; Li, Q. H. Chin. J. Org. Chem. 2009, 29, 993 (in Chinese).
(叶英, 赵志刚, 刘兴利, 李清寒, 有机化学, 2009, 29, 993.)
[7] Sharma, K.; Jain, R.; Joshi, K. C. Indian J. Heterocycl. Chem. 1992, 29, 189.
[8] Brudeli, B.; Moltzau, L. R.; Andressen, K. W.; Krobert, K. A.; Klaveness, J.; Levy, F. O. Bioorg. Med. Chem. 2010, 18, 8600.
[9] Zhang, Y. B. World Pestic. 2009, 31, 54 (in Chinese).
(张亦冰. 世界农药, 2009, 31, 54.)
[10] Liu, L.; Zheng, Z. B.; Qin, Z. H.; Fu, B.; Yuan, H. Z. Chin. J. Org. Chem. 2008, 28, 1841 (in Chinese).
(刘磊, 郑中博, 覃兆海, 傅滨, 袁会珠, 有机化学, 2008, 28, 1841.)
[11] Park, H.-J.; Lee, K.; Park, S.-J.; Ahn, B.; Lee, J.-C.; Cho, H.-Y.; Lee, K.-I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[12] 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.)
[13] Jiang, L.; Wang, H. B.; Mu W.; Ji, Z. C; Cao, P. Chin. J. Chem. 2011, 29, 539.
[14] Jiang, L. L.; Chen, C. N.; Zhou, Y. F.; Chen, Q.; Yang, G. F. Chin. J. Org. Chem. 2009, 29, 1392 (in Chinese).
(江黎黎, 陈超南, 周延菲, 陈琼, 杨光富, 有机化学, 2009, 29, 1392.)
[15] Uncuta, C.; Tudose, A.; Caproiu, M. T.; Udrea, S.; Roussel, C. Eur. J. Org. Chem. 2003, 38, 1789.
[16] Liu, Z. J.; Zhang, J. H.; Jiang, L. Chem. J. Chin. Univ. 1991, 12, 39 (in Chinese).
(刘志杰, 张建恒, 姜林, 高等学校化学学报, 1991, 12, 39.)
[17] Li, X. H.; Ji, M. S.; Qi, Z. Q.; Li, X. W.; Shen, Y. X.; Gu, Z. M.; Zhang, Y.; Wei, S. H.; Wang, Y. Z.; Wang, D. Q. Pest Manage. Sci. 2011, 67, 986.
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