4-[[[(ferrocenylamino)carbonyl]oxy]methyl]-phenol acetate | 1398039-52-5

• 英文名称: 4-[[[(ferrocenylamino)carbonyl]oxy]methyl]-phenol acetate
• CAS: 1398039-52-5
• 化学式: C₂₀H₁₉FeNO₄
• 分子量: 393.222
• InChiKey: SLMHVIMKEBHUEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  对硝基苯基对乙酰氧基苄基碳酸酯 、 氨基二茂铁 以 四氢呋喃 为溶剂， 反应 77.0h， 生成 4-[[[(ferrocenylamino)carbonyl]oxy]methyl]-phenol acetate
  参考文献：
  名称：

  [EN] FERROCENE-BASED COMPOUNDS AND THEIR USE AS ROS REGULATING PRODRUGS
  [FR] COMPOSÉS À BASE DE FERROCÈNE ET LEUR UTILISATION COMME PROMÉDICAMENTS RÉGULANT LES ESPÈCES RÉACTIVES DE L'OXYGÈNE (ROS)

  摘要：

  本发明涉及基于二茂铁的化合物及其作为活性氧（ROS，反应性氧种）调节前药的使用。特别是，本发明涉及在激活时作为增加细胞氧化应激的ROS调节前药的基于二茂铁的化合物。

  公开号：

  WO2012123076A1

文献信息

• Aminoferrocene-Based Prodrugs and Their Effects on Human Normal and Cancer Cells as Well as Bacterial Cells
  作者：Paul Marzenell、Helen Hagen、Leopold Sellner、Thorsten Zenz、Ruta Grinyte、Valeri Pavlov、Steffen Daum、Andriy Mokhir

  DOI：10.1021/jm400754c

  日期：2013.9.12

  Aminoferrocene-based prodrugs are activated under cancer-specific conditions (high concentration of reactive oxygen species, ROS) with the formation of glutathione scavengers (p-quinone methide) and ROS-generating iron complexes. Herein, we explored three structural modifications of these prodrugs in an attempt to improve their properties: (a) the attachment of a -COOH function to the ferrocene fragment leads to the improvement of water solubility and reactivity in vitro but also decreases cell-membrane permeability and biological activity, (b) the alkylation of the N-benzyl residue does not show any significant affect, and (c) the attachment of the second arylboronic acid fragment improves the toxicity (IC50) of the prodrugs toward human promyelocytic leukemia cells (HL-60) from 52 to 12 mu M. Finally, we demonstrated that the prodrugs are active against primary chronic lymphocytic leukemia (CLL) cells, with the, best compounds exhibiting an IC50 value of 1.5 mu M. The most active compounds were found to not affect mononuclear cells and representative bacterial cells.