1-amino-1′-methoxycabonyl-ferrocene hydrochloride | 1292282-67-7

• 英文名称: 1-amino-1′-methoxycabonyl-ferrocene hydrochloride
• CAS: 1292282-67-7
• 化学式: C₁₂H₁₃FeNO₂*ClH
• 分子量: 295.549
• InChiKey: DDSQFPBABRKBJK-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：
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• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-amino-1′-methoxycabonyl-ferrocene hydrochloride 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以99%的产率得到1-amino-1′-methoxycarbonylferrocene
  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
• 作为产物：
  描述：

  tert-butyl 1′-methoxycarbonylferrocene-1-carbamate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-amino-1′-methoxycabonyl-ferrocene hydrochloride
  参考文献：
  名称：

  1'-氨基二茂铁-1-羧酸和脯氨酸的结合物：合成、构象分析和生物学评价

  摘要：

  我们之前的研究表明，二肽 Y-Fca-Ala-OMe (III) 转变为 Y-Ala-Fca-OMe (IV)（Y = Ac，Boc；Fca = 1'-aminoferrocene-1-羧酸）显着影响它们的构象空间。新的生物偶联物 Y-Fca-Pro-OMe (1, Y = Ac; 2, Y = Boc) 和 Y-Pro-Fca-OMe (3, Y = Boc; 4, Y = Ac)研究脯氨酸（一种众所周知的转角诱导剂）对具有交换组成氨基酸序列的小有机金属肽的构象特性的影响。为此，肽 1-4 在溶液中进行了详细的光谱分析（IR、NMR、CD 光谱）。测定了固态中肽 3 的构象。此外，

  DOI：

  10.3390/molecules190812852

文献信息

• The first oxalamide-bridged ferrocene: Facile synthesis, preliminary conformational analysis and biological evaluation
  作者：Veronika Kovač、Kristina Radošević、Anica Bebek、Janja Makarević、Zoran Štefanić、Lidija Barišić、Mladen Žinić、Vladimir Rapić

  DOI：10.1002/aoc.3653

  日期：2017.7

  so‐obtained oxalamide‐bridged ferrocene 2 was elucidated using infrared and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopies, crystal structure analysis, and electrospray ionization and high‐resolution mass spectrometry. The preliminary conformational analysis in solution suggested the intramolecular engagement of oxalamide protons, while single‐crystal analysis revealed an intermolecular hydrogen‐bonding

  对叔丁基1'-甲氧基羰基-1-二茂铁氨基甲酸酯（1）进行Boc脱保护，得到游离胺，该胺经过草酰氯介导的二聚作用。使用红外光谱和NMR（1 H，13 C，COSY，NOESY，HSQC，HMBC）光谱学，晶体结构分析以及电喷雾电离和高分辨率质谱对得到的草酰胺桥二茂铁2的结构进行了阐明。溶液中的初步构象分析表明草酰胺的质子在分子内参与，而单晶分析揭示了分子间的氢键模式。另外，草酰胺桥二茂铁2的作用对三种人类细胞系（HEK293T，HeLa和HepG2）的细胞活力进行了测试。体外筛选显示，在所应用的浓度范围（1-350μM）中，测试化合物对HEK293T和HepG2细胞具有增殖和细胞毒性作用。正常HEK293T细胞对细胞生长的刺激作用最为明显，而对HeLa肿瘤细胞的细胞毒性作用最高，且呈剂量依赖性。观察到的双重生物活性2暗示其在药物开发中的潜在应用。
• Ferrocenyl-Labeled Sugar Amino Acids: Conformation and Properties
  作者：Christoph Förster、Monika Kovačević、Lidija Barišić、Vladimir Rapić、Katja Heinze

  DOI：10.1021/om300174p

  日期：2012.5.14

  Novel organometallic sugar amino acid conjugates 1-5 have been prepared by amide coupling of O-protected N-acetylmuramic acid and iso-muramic acid (2-[3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid) with 1-aminoferrocene, 1'-aminoferrocene-1'-carboxylic acid (H-Fca-OH), or 1,1'-diaminoferrocene, respectively. The influence of the ferrocenyl moiety and presence of additional remote potential hydrogen atom acceptors and donors at the ferrocenyl core on the conformation and lipophilicity is investigated by TLC, IR, NMR, and CD spectroscopic methods augmented by density functional calculations. Furthermore, the redox potential of the ferrocene/ferrocenium couple is tuned by the electron-withdrawing and -donating nature of the substituents at the ferrocenyl label.