Chinese Journal of Organic Chemistry >
Design, Synthesis and Biological Activity of Novel (3-Substituted phenyl-2-propen-1-ylidene)-benzoylhydrazones
Received date: 2014-01-20
Revised date: 2014-02-19
Online 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).
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
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]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1118 -1123 . DOI: 10.6023/cjoc201401034
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