2-(N,N-dimethylaminomethyl)ferrocenecarboxamide | 1015229-61-4

• 英文名称: 2-(N,N-dimethylaminomethyl)ferrocenecarboxamide
• CAS: 1015229-61-4
• 化学式: C₁₄H₁₈FeN₂O
• 分子量: 286.157
• InChiKey: SVGOBRAMSHYUGO-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：
  None
• sp3杂化的碳原子比例：
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• 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：

  2-(N,N-dimethylaminomethyl)ferrocenecarboxamide 、 碘甲烷 以 乙醚 、 乙腈 为溶剂， 以87%的产率得到N,N,N-trimethyl-N-(2-carbamoylferrocenylmethyl)ammonium iodide hydrate
  参考文献：
  名称：

  Synthesis, characterization and antitumor activity of 1,2-disubstituted ferrocenes and cyclodextrin inclusion complexes

  摘要：

  Seven different ferrocene derivatives have been tested in vitro against Ehrlich ascites tumor cells. Neither ferrocene nor the monosubstituted derivative N, N-dimethylaminomethylferrocene showed cytotoxic activity (IC(50) > 1000 mu M for 3 h treatments). Better results were obtained with 1,2-disubstituted derivatives. The IC(50) values ranged from 376.6 mu M for 1,2-diformylferrocene to 71.2 mu M for racemic 2-( N, N-dimethylaminomethyl) ferrocenecarboxamide. The latter derivative was also encapsulated in native beta-cyclodextrin ( CD), heptakis-2,3, 6-tri-O-methyl-beta-CD (TRIMEB) and 2-hydroxypropyl-beta-CD (HP beta CD) to give 1: 1 (host: guest) inclusion compounds. The existence of true inclusion complexes in the solid state was confirmed by a combination of powder X-ray diffraction, thermogravimetric analysis, FTIR and (13)C CP MAS NMR spectroscopy. The IC(50) value for the beta-CD inclusion compound was identical to that obtained for the nonincluded ferrocene derivative. By contrast, the inclusion compounds comprising TRIMEB and HP beta CD yielded IC(50) values of 25.2 and 20.0 mu M, respectively. No obvious relationship could be established between the redox behavior of the compounds determined by cyclic voltammetry and the biochemical data. (c) 2007 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.11.053
• 作为产物：
  描述：

  N,N-dimethylaminomethylferrocene 、 二氧化碳 、 氨 在 草酰氯 、 叔丁基锂 、 三氟乙酸 作用下， 以 乙醚 、 乙腈 为溶剂， 以63%的产率得到2-(N,N-dimethylaminomethyl)ferrocenecarboxamide
  参考文献：
  名称：

  Synthesis, characterization and antitumor activity of 1,2-disubstituted ferrocenes and cyclodextrin inclusion complexes

  摘要：

  Seven different ferrocene derivatives have been tested in vitro against Ehrlich ascites tumor cells. Neither ferrocene nor the monosubstituted derivative N, N-dimethylaminomethylferrocene showed cytotoxic activity (IC(50) > 1000 mu M for 3 h treatments). Better results were obtained with 1,2-disubstituted derivatives. The IC(50) values ranged from 376.6 mu M for 1,2-diformylferrocene to 71.2 mu M for racemic 2-( N, N-dimethylaminomethyl) ferrocenecarboxamide. The latter derivative was also encapsulated in native beta-cyclodextrin ( CD), heptakis-2,3, 6-tri-O-methyl-beta-CD (TRIMEB) and 2-hydroxypropyl-beta-CD (HP beta CD) to give 1: 1 (host: guest) inclusion compounds. The existence of true inclusion complexes in the solid state was confirmed by a combination of powder X-ray diffraction, thermogravimetric analysis, FTIR and (13)C CP MAS NMR spectroscopy. The IC(50) value for the beta-CD inclusion compound was identical to that obtained for the nonincluded ferrocene derivative. By contrast, the inclusion compounds comprising TRIMEB and HP beta CD yielded IC(50) values of 25.2 and 20.0 mu M, respectively. No obvious relationship could be established between the redox behavior of the compounds determined by cyclic voltammetry and the biochemical data. (c) 2007 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.11.053