Synthesis and Biological Activity of Oxime Ethers of Curcumin Derivatives

doi:10.6023/cjoc201402035

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (8): 1662-1668.DOI: 10.6023/cjoc201402035 Previous Articles Next Articles

Notes

含肟醚的姜黄素衍生物的合成及生物活性研究

陈玉, 王忠波, 张贤, 夏丽娟, 龚华玉, 赵洪菊, 薛伟

贵州大学精细化工研究开发中心绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与生物工程重点实验室贵阳 550025

收稿日期:2014-02-27 修回日期:2014-04-30 发布日期:2014-05-05
通讯作者: 薛伟 E-mail:wxue@gzu.edu.cn
基金资助:
国家十二五科技支撑计划（No.2011BAE06B04-09）和贵州大学研究生创新基金（No.2013036）资助项目.

Synthesis and Biological Activity of Oxime Ethers of Curcumin Derivatives

Chen Yu, Wang Zhongbo, Zhang Xian, Xia Lijuan, Gong Huayu, Zhao Hongju, Xue Wei

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Bioengineering of Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2014-02-27 Revised:2014-04-30 Published:2014-05-05
Supported by:
Project supported by the National Tweifth Five-Year Plan for Science and Technology (No. 2011BAE06B04-09) and the Innovation Fund for Graduate Student of Guizhou University (No. 2013036)

1. Synthesis and Biological Activity of Oxime Ethers of Curcumin Derivatives.PDF(2632KB)

Abstract

On the principle of biologically active factor splicing, curcumin derivatives introduced active functional group oxime ethers into the structure of 1,4-pentadien-3-one. A series of new 1-phenyl-5-heterocycle-1,4-pentadien-3-one oxime ethers were synthesized, and their structures were identified by IR, ¹H NMR, ¹³C NMR, ESI-MS and elemental analysis. The preliminary bioassay results indicated that target compounds showed certain antiviral activity against TMV at a concentration of 500 μg/mL.

Key words: curcumin, oxime ether, synthesis, anti-TMV activity

Cite this article

Chen Yu, Wang Zhongbo, Zhang Xian, Xia Lijuan, Gong Huayu, Zhao Hongju, Xue Wei. Synthesis and Biological Activity of Oxime Ethers of Curcumin Derivatives[J]. Chin. J. Org. Chem., 2014, 34(8): 1662-1668.

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[1] Kumar, S.; Narain, U.; Tripathi, S.; Misra, K. Bioconjugate Chem. 2001, 12, 464.
[2] Toshiya, M.; Kayo, H.; Ayumi, S. Agric. Food. Chem. 1999, 47, 1.
[3] Ammon, H.; Wahl, M. Planta Med. 1991, 57, 1.
[4] Hahm, E. R.; Cheon, G.; Lee, J.; Kim, B.; Park, C.; Yang, C. H. Cancer Lett. 2002, 184, 89.
[5] Costi, R.; Santo, R. D.; Artico, M.; Massa, S.; Ragno, R.; Loddo, R.; Colla, M. L.; Tramontano, E.; Colla, P. L.; Pani, A. Bioorg. Med. Chem. 2004, 12, 199.
[6] Wang, D. S.; Yang, C. M.; Liu, X. P. J. Nat. Sci. Hunan Normal Univ. 2005, 28, 56 (in Chinese).
(王胜得, 杨春明, 刘兴平, 湖南师范大学自然科学学报, 2005, 28, 56).
[7] Jiang, L.; Wang, H. B.; Mu, W.; Ji, Z. C.; Cao, P. Chin. J. Chem. 2011, 29, 539.
[8] Yang, S.; Song, B. A.; Liu, X. H. Chin. J. Org. Chem. 2005, 25, 1116 (in Chinese).
(杨松, 宋宝安, 刘新华, 有机化学, 2005, 25, 1116.)
[9] Li, S. B.; Hu, D. Y.; Song, B. A.; Yang, S.; Jin, L. H.; Xue, W.; Zeng, S.; Wang, J.; Chen, Z.; Lu, P.; Zhou, X.; Fan, L. E. Chin. J. Org. Chem. 2008, 28, 311 (in Chinese).
(李少博, 胡德禹, 宋宝安, 杨松, 金林红, 薛伟, 曾松, 王俊, 陈卓, 卢平, 周霞, 樊玲娥, 有机化学, 2008, 28, 311.)
[10] Wang, Z. N.; Hu, D. Y.; Song, B. A.; Yang, S.; Jin, L. H.; Xue, W. Chin. J. Org. Chem. 2009, 29, 1412 (in Chinese).
(王振宁, 胡德禹, 宋宝安, 杨松, 金林红, 薛伟, 有机化学, 2009, 29, 1412.)
[11] Chen, P. L. M.S. Thesis, Guizhou University, Guiyang, 2010 (in Chinese).
(陈鹏丽, 硕士论文, 贵州大学, 贵阳, 2010.)
[12] Qiu, Q. J.; Xue, W.; Lu, P.; Wang, Z. C.; Wei, X. Chin. J. Synth. Chem. 2011, 19, 36 (in Chinese).
(仇秋娟, 薛伟, 卢平, 王贞超, 魏学, 合成化学, 2011, 19, 36.)
[13] Ma, X. B.; Yin, A. Q.; Xue, S. J. J. Shanghai Normal Univ. (Nat. Sci. 2011, 40, 41.
[14] Sun, G. C.; Chang, J. B.; Chen, R. F.; Xie, J. X.; Cheng, G. F.; Wang, L. F.; He, J.; Wang, L. M. Chin. J. Appl. Chem. 2002, 19, 621 (in Chinese).
(孙纲春, 常俊标, 陈荣锋, 谢晶曦, 程桂芳, 王流芳, 何娟, 王利敏, 应用化学, 2002, 19, 621.)
[15] Li, S. Z.; Wang, D. H.; Jiao, S. M.; Cheng, S. E. Pesticide Experiment Methods——Fungicide Sector, Agriculture Press of China, Beijing, 1991, p. 93 (in Chinese).
(李树正, 王笃祜, 焦书梅, 程书恩, 农药实验法: 杀菌剂篇, 农业出版社, 北京, 1991, p. 93.)
[16] Kong, F. B.; Gao, Y. F.; Chen, X. L.; Li, G. L.; Chen, J. Guangxi Agric. Sci. 2006, 37, 148 (in Chinese).
(孔凡彬, 高扬帆, 陈锡岭, 李广领, 陈军, 广西农业科学, 2006, 37, 148.)

含肟醚的姜黄素衍生物的合成及生物活性研究

Synthesis and Biological Activity of Oxime Ethers of Curcumin Derivatives

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