| 1452506-22-7

• CAS: 1452506-22-7
• 化学式: C₄₀H₅₀B₂FeN₂O₈
• 分子量: 764.315
• InChiKey: VCORFZIKFXPDTI-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：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  1,1'-diisocyanatoferrocene 、 4-(hydroxymethyl)-2-methylphenylboronic acid pinacol ester 以 二氯甲烷 为溶剂， 反应 22.0h， 以185 mg的产率得到
  参考文献：
  名称：

  Aminoferrocene-Based Prodrugs and Their Effects on Human Normal and Cancer Cells as Well as Bacterial Cells

  摘要：

  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.

  DOI：

  10.1021/jm400754c