Design, Synthesis and Biological Activity of Novel (3-Substituted phenyl-2-propen-1-ylidene)-benzoylhydrazones

doi:10.6023/cjoc201401034

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1118-1123.DOI: 10.6023/cjoc201401034 Previous Articles Next Articles

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新型(3-取代苯基-2-丙烯-1-亚基)-苯甲酰腙类化合物的设计、合成及生物活性研究

徐焱, 雷鹏, 凌云, 王圣文, 杨新玲

中国农业大学理学院应用化学系农业部农药化学及应用重点开放实验室北京 100193

收稿日期:2014-01-20 修回日期:2014-02-19 发布日期:2014-03-12
通讯作者: 杨新玲 E-mail:yangxl@cau.edu.cn
基金资助:
国家重点基础研究发展计划（No. 2010CB126104）和国家“十二五”科技支撑计划课题（No. 2011BAE06B05-5）资助项目.

Design, Synthesis and Biological Activity of Novel (3-Substituted phenyl-2-propen-1-ylidene)-benzoylhydrazones

Xu Yan, Lei Peng, Ling Yun, Wang Shengwen, Yang Xinling

Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193

Received:2014-01-20 Revised:2014-02-19 Published:2014-03-12
Supported by:
Project supported by the National Basic Research Program of China (No. 2010CB126104) and the National “Twelfth Five-Year” Plan for Science & Technology (No. 2011BAE06B05-5).

1. Design, Synthesis and Biological Activity of Novel (3-Substituted phenyl-2-propen-1-ylidene)-benzoylhydrazones.PDF(3660KB)

Abstract

To find new lead compound with high fungicidal activity, a series of novel (3-substituted phenyl-2-propen-1- ylidene)-benzoylhydrazones were designed via the method of linking active sub-structures which were cinnamaldehyde and benzoylhydrazine. The target compounds were synthesized from substituted benzoic acid in three steps. Their structures were confirmed by ¹H NMR, IR spectra and elemental analysis. The in vitro bioassay results indicated that some target compounds showed obvious inhibitory activities against mushroom tyrosinase compared with lead cinnamaldehyde. Besides, some target compounds exhibit certain fungicidal activity against Fusarium graminearum, Botrytis cinerea and Colletotrichum lagenarium. Compound 5r exhibited equivalent fungicidal activities to polyoxin B at a concentration of 100 μg/mL. The preliminary structure-activity relationship was also analyzed for further optimization.

Key words: cinnamaldehyde, benzoylhydrazone, synthesis, tyrosinase, antifungal activity

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Xu Yan, Lei Peng, Ling Yun, Wang Shengwen, Yang Xinling. Design, Synthesis and Biological Activity of Novel (3-Substituted phenyl-2-propen-1-ylidene)-benzoylhydrazones[J]. Chin. J. Org. Chem., 2014, 34(6): 1118-1123.

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新型(3-取代苯基-2-丙烯-1-亚基)-苯甲酰腙类化合物的设计、合成及生物活性研究

Design, Synthesis and Biological Activity of Novel (3-Substituted phenyl-2-propen-1-ylidene)-benzoylhydrazones

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