有机化学 ›› 2013, Vol. 33 ›› Issue (05): 1005-1009.DOI: 10.6023/cjoc201212025 上一篇    下一篇

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   

  1. 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 发布日期:2013-01-23
  • 通讯作者: 姜林,jiangl@sdau.edu.cn E-mail:jiangl@sdau.edu.cn
  • 基金资助:

    山东省自然科学基金(No. ZR2009BM044)资助项目.

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   

  1. College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018
  • Received:2012-12-16 Revised:2013-01-20 Published:2013-01-23
  • Supported by:

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

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3a3j, 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3f3g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

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 3a3j, 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