7-methoxy-2-ferrocenyl-chromen-4-one | 1332699-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-methoxy-2-ferrocenyl-chromen-4-one
• 英文别名: cyclopenta-1,3-diene;2-cyclopenta-2,4-dien-1-yl-7-methoxychromen-4-one;iron(2+)
• CAS: 1332699-60-1
• 化学式: C₂₀H₁₆FeO₃
• 分子量: 360.192
• InChiKey: FWGCLYLEJDPLOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-2-[(ferrocenyl)methylidene]-6-methoxy-1-benzofuran-3(2H)-one 在 potassium cyanide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以49%的产率得到7-methoxy-2-ferrocenyl-chromen-4-one
  参考文献：
  名称：

  二茂铁嵌入的类黄酮通过附带敏感性靶向多重耐药性癌细胞的致命弱点。

  摘要：

  为了开发选择性对抗耐药肿瘤细胞的抗癌药，我们研究了嵌入查耳酮，金酮和黄酮骨架中的二茂铁。构想了这些化合物，然后根据附带敏感性的概念进行了研究，其中的靶标是过度表达多药ABC转运蛋白MRP1的癌细胞的跟腱。评价了14种合成化合物从过表达MRP1的肿瘤细胞中诱导谷胱甘肽（GSH）外排的能力。当在5和20μM下进行测试时，发现每个系列中的至少一种化合物是GSH外排的高度诱导剂。分别在敏感和耐药细胞系上评估了诱导GSH高流出的不同化合物，发现其中两种属于黄酮类，对耐药癌细胞具有更高的细胞毒性，最佳选择比> 9.1。我们的结果为进一步优化奠定了化学和生物学基础。

  DOI：

  10.1016/j.ejmech.2017.02.064

文献信息

• Ferrocenyl flavonoid-induced morphological modifications of endothelial cells and cytotoxicity against B16 murine melanoma cells
  作者：Jean-Philippe Monserrat、Keshri Nath Tiwari、Lionel Quentin、Pascal Pigeon、Gérard Jaouen、Anne Vessières、Guy G. Chabot、Elizabeth A. Hillard

  DOI：10.1016/j.jorganchem.2012.12.031

  日期：2013.6

  With the aim of improving the cytotoxic and vascular disrupting activities of flavonoids, several classes of ferrocenyl-modified flavonoids were prepared and tested on cancer and endothelial cells. Three tenmember series of ferrocenyl flavonoids: chalcones ((E)-1-(R-2'-hydroxypheny1)-3-ferrocenylprop-2-en-1-ones), aurones ((Z)-R-2-(ferrocenylidene)benzofuran-3-ones) and flavones (R-2-ferrocenyl-chromen-4-ones) were synthesized by recently reported methods. Three ferrocenyl flavonols (R-3-hydroxy2-ferrocenyl-chromen-4-ones) and four ferrocenyl flavanones (3-ferrocenylmethylidenyl-R-2-phenyl-chroman-4-ones) were also obtained. All compounds were evaluated for their cytotoxic effects on a cancer cell line (B16 murine melanoma) and for their morphological effects on endothelial cells (EAhy 926). Some interesting structure-activity relationships were disclosed: of all the compounds, the halogen-substituted aurones showed the best cytotoxic activity, with IC50 values ranging between 12 and 18 mu M. Ferrocenyl flavonols and ferrocenyl flavanones with substitution in the 3-position (-OH and =C-Fc respectively) were not active against cancer or endothelial cells. Some of the ferrocenyl flavones caused the endothelial cells to adopt a round shape ("rounding up") at submicromolar concentrations, which can be predictive of vascular disrupting activity. The most morphologically active flavones showed only moderate cytotoxicity against cancer cells, indicating that they may primarily act as antivascular agents. (C) 2013 Elsevier B.V. All rights reserved.
• Ferrocenyl-Appended Aurone and Flavone: Which Possesses Higher Inhibitory Effects on DNA Oxidation and Radicals?
  作者：Jia-Feng Chen、Zai-Qun Liu

  DOI：10.1021/tx500405b

  日期：2015.3.16

  The aim of the present work was to compare the antioxidative effect of the ferrocenyl-appended aurone with that of ferrocenyl-appended flavone; therefore, nine aurones together with the flavone-type analogues were synthesized by using chalcone as the reactant. The radical-scavenging property was evaluated by reacting with the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS'), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. The cytotoxicity was estimated by inhibiting 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that the introduction of the ferrocenyl group remarkably increased the radical-scavenging activities of aurone and flavone. Especially, the ferrocenyl group in flavones can quench radicals even in the absence of the phenolic hydroxyl group, while ferrocenyl-appended aurones can efficiently protect DNA against AAPH-induced oxidation. Therefore, the antioxidative effect was generated by the ferrocenyl group and enhanced by the electron-donating group attaching to the para-position of the ferrocenyl group. Introducing the ferrocenyl group into natural compounds may be a useful strategy for increasing the anticoddative effectiveness.