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
收稿日期: 2014-01-20
修回日期: 2014-02-19
网络出版日期: 2014-03-12
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
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).
徐焱 , 雷鹏 , 凌云 , 王圣文 , 杨新玲 . 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[J]. 有机化学, 2014 , 34(6) : 1118 -1123 . DOI: 10.6023/cjoc201401034
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
[1] Hearing, V. -J.; Tsukamoto, K. FASEB J. 1991, 5, 2902
[2] Oetting, W.-S. Pigm. Cell Res. 2000, 13, 3205
[3] Barrett, F.-M. Can. J. Zool. 1984, 62, 834
[4] Sugumaran, M. FEBS Lett. 1991, 293, 4
[5] Friedman, M. J. Agric. Food Chem. 1996, 44, 631
[6] Kubo, I.; Kinst-Hori, I. J. Agric. Food Chem. 1998, 46, 1268
[7] Kubo, I.; Kinst-Hori, I. J. Agric. Food Chem. 1998, 46, 5338
[8] Kubo, I.; Kinst-Hori, I. J. Agric. Food Chem. 1999, 47, 4574
[9] Lee, H.-C.; Cheng, S.-S.; Chang, S.-T. J. Sci. Food Agric. 2005, 85, 2047.
[10] Didry, N.; Dubreuil, L.; Pinkas, M. Pharmazie 1993, 48, 301.
[11] Imai, T.; Yasuhara, K.; Tamura, T.; Takizawa, T.; Ueda, M.; Hirose, M.; Mitsumori, K. Cancer Lett. 2002, 175, 9.
[12] Huang, J.; Cui, Z.-N.; Li, Y.; Yang, X.-L. Chin. J. Org. Chem. 2008, 28, 598 (in Chinese).
(黄娟, 崔紫宁, 李映, 杨新玲, 有机化学, 2008, 28, 598.)
[13] Wang, Z.; Dong, W.; Xu, Y.; Liang, P.; Yang, X. -L. Chin. J. Pestic. Sci. 2010, 12, 264 (in Chinese).
(王振, 董玮, 徐焱, 梁沛, 杨新玲, 农药学学报, 2010, 12, 264.)
[14] Xu, Y.; Wang, Z.; Ling, Y.; Dong, W.; Xing, J.; Liang, P.; Yang, X.-L. Chin. J. Org. Chem. 2012, 32, 1278 (in Chinese).
(徐焱, 王振, 凌云, 董玮, 邢静, 梁沛, 杨新玲, 有机化学, 2012, 32, 1278.)
[15] Cui, Z.-N.; Shi, Y.-X.; Zhang, L.; Ling, Y.; Li, B.-J.; Nishida, Y.; Yang, X.-L. J. Agric. Food Chem. 2012, 60, 11649
[16] Cui, Z.-N.; Zhang, L.; Huang, J.; Ling, Y.; Yang, X.-L. Chin. J. Org. Chem. 2010, 30, 1482 (in Chinese).
(崔紫宁, 张莉, 黄娟, 凌云, 杨新玲, 有机化学, 2010, 30, 1482.)
[17] Hearing, V.-J. Methods in Enzymology, Academic Press, New York, 1987, 142, 154.
[18] Chen, N. C. Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, p. 161 (in Chinese).
(陈年春, 农药生物测定技术, 北京农业大学出版社, 北京, 1991, p. 161.)
[19] Deng, G.-M.; Chen, Z.; Wang, C.-R.; Zhang, H. M. Acta Crystallogr., E 2012, 68, o160.
/
| 〈 |
|
〉 |
