Synthesis and Properties of 4-Ferrocenyl-carboxybenzenecoumarin Derivatives

doi:10.6023/cjoc201611036

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2008-2014.DOI: 10.6023/cjoc201611036 Previous Articles Next Articles

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二茂铁苯甲酸香豆素类化合物的合成与性质研究

李标^a, 刘秋霞^b, 周元清^a, 贾赵栋^a, 朱曼毓^a, 徐琰^a, 宋毛平^a

a 郑州大学化学与分子工程学院郑州 450001;
b 洛阳师范学院化学化工学院洛阳 471000

收稿日期:2017-01-10 修回日期:2017-04-07 发布日期:2017-04-21
通讯作者: 徐琰 E-mail:xuyan@zzu.edu.cn
基金资助:
国家自然科学基金（No.21171149）资助项目.

Synthesis and Properties of 4-Ferrocenyl-carboxybenzenecoumarin Derivatives

Li Biao^a, Liu Qiuxi^b, Zhou Yuanqing^a, Jia Zhaodong^a, Zhu Manyu^a, Xu Yan^a, Song Maoping^a

a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
b College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471000

Received:2017-01-10 Revised:2017-04-07 Published:2017-04-21
Contact: 10.6023/cjoc201611036 E-mail:xuyan@zzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21171149).

1. Synthesis and Properties of 4-Ferrocenyl-carboxybenzenecoumarin Derivatives.PDF(1636KB)

Abstract

Six novel ferrocenyl-carboxybenzene-coumarin derivatives were synthesized by 4-ferrocenylbenzoic and coumarin as raw materials through nitration, reduction reaction and condensation. The structures of compounds were characterized by IR, ¹H NMR, ¹³C NMR and elemental analysis. The crystal structure of 4-ferrocene benzoic acid(coumarin-4-yl) ester (FcL₁) was determined by X-ray diffraction analysis. The electrochemical research showed that the redox reaction on the surface of electrode was reversible with single electron and controlled by diffusion. Biological activity test results showed that the compound modified not conducive to the improvement of the bactericidal activity, only beneficial to the improvement of the antitumor activity. All the six compounds showed good inhibition against Curvularia lunata and Fusarium graminearum. In addition, FcL₁ and 4-ferrocene benzoic acid (coumarin-7-yl) ester (FcL₂) exhibited significant activities and selectivities against Esophageal carcinoma cell (IC₅₀ value=2.10 and 1.25 μmol/L, respectively) in the anticancer activity test.

Key words: ferrocene, coumarin, electrochemical research, biological activity

Cite this article

Li Biao, Liu Qiuxi, Zhou Yuanqing, Jia Zhaodong, Zhu Manyu, Xu Yan, Song Maoping. Synthesis and Properties of 4-Ferrocenyl-carboxybenzenecoumarin Derivatives[J]. Chin. J. Org. Chem., 2017, 37(8): 2008-2014.

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二茂铁苯甲酸香豆素类化合物的合成与性质研究

Synthesis and Properties of 4-Ferrocenyl-carboxybenzenecoumarin Derivatives

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