| 1452506-19-2

• CAS: 1452506-19-2
• 化学式: C₃₈H₄₆B₂FeN₂O₈
• 分子量: 736.261
• InChiKey: GWHCKQLNIGEYEA-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  、 氯化苄 在 四丁基碘化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以55%的产率得到
  参考文献：
  名称：

  Improved Synthesis of N-Benzylaminoferrocene-Based Prodrugs and Evaluation of Their Toxicity and Antileukemic Activity

  摘要：

  We report on an improved method of synthesis of N-benzylaminoferrocene-based prodrugs and demonstrate its applicability by preparing nine new aminoferrocenes. Their effect on the viability of selected cancer cells having different p53 status was studied. The obtained data are in agreement with the hypothesis that the toxicity of aminoferrocenes is not dependent upon p53 status. Subsequently the toxicity of a selected prodrug (4) was investigated ex vivo using rat precision cut liver slices and in vivo on hybrid male mice BDF1. In both experiments no toxicity was observed: ex vivo, up to 10 mu M; in vivo, up to 6 mg/kg. Finally, prodrug 4 was shown to extend the survival of BDF1 mice carrying L1210 leukemia from 13.7 +/- 0.6 days to 17.5 +/- 0.7 days when injected daily 6 times at a dose of 26 mu g/kg starting from the second day after injection of L1210 cells.

  DOI：

  10.1021/jm5019548
• 作为产物：
  描述：

  1,1'-diisocyanatoferrocene 、 4-(羟甲基)苯硼酸频哪醇酯 以 二氯甲烷 为溶剂， 反应 22.0h， 以162 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