有机化学 ›› 2017, Vol. 37 ›› Issue (8): 2008-2014.DOI: 10.6023/cjoc201611036 上一篇    下一篇

研究论文

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   

  1. 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 出版日期:2017-08-25 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 Biaoa, Liu Qiuxib, Zhou Yuanqinga, Jia Zhaodonga, Zhu Manyua, Xu Yana, Song Maopinga   

  1. 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 Online:2017-08-25 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).

以二茂铁苯甲酸、香豆素为原料,经硝化、硝基还原和缩合等反应,设计、合成了6个新型的二茂铁苯甲酸香豆素化合物.采用红外、元素分析和核磁共振对化合物进行表征.用X射线单晶衍射测定了4-二茂铁苯甲酸(香豆素-4-基)酯(FcL1)的晶体结构.研究了这6种化合物的电化学性质和生物活性.电化学研究表明这6种物质在电极表面均可发生可逆的单电子氧化还原反应,且反应受扩散控制.生物活性测试结果表明化合物的修饰不利于杀菌活性的改善,仅有利于抗肿瘤活性的提高.其中这6种化合物对新月弯孢霉菌和玉米禾谷镰刀菌都具有较好的杀菌活性,化合物FcL1和4-二茂铁苯甲酸(香豆素-7-基)酯(FcL2)对人食管癌细胞9706 (EC-9706)的IC50分别可达到2.10和1.25 μmol/L.

关键词: 二茂铁, 香豆素, 电化学性质, 生物活性

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