2-(4-nitro-1H-imidazol-1-yl)ethanamine hydrochloride | 80087-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-nitro-1H-imidazol-1-yl)ethanamine hydrochloride
• 英文别名: 2-(4-nitroimidazol-1-yl)ethanamine;hydrochloride
• CAS: 80087-84-9
• 化学式: C₅H₈N₄O₂*ClH
• 分子量: 192.605
• InChiKey: SKBDJXCWFPOAJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-nitro-1H-imidazolyl)butanoic acid 、 2-(4-nitro-1H-imidazol-1-yl)ethanamine hydrochloride 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到N-[2-(4-nitro-1H-imidazolyl)ethyl]-4-(2-nitro-1H-imidazolyl)butanamide
  参考文献：
  名称：

  Hay; Wilson; Moselen, Journal of Medicinal Chemistry, 1994, vol. 37, # 3, p. 381 - 391

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[2-(4-nitro-imidazol-1-yl)-ethyl]-phthalimide 在 肼 作用下， 以61.7%的产率得到2-(4-nitro-1H-imidazol-1-yl)ethanamine hydrochloride
  参考文献：
  名称：

  99mTc/Re complexes bearing bisnitroimidazole or mononitroimidazole as potential bioreductive markers for tumor: Synthesis, physicochemical characterization and biological evaluation

  摘要：

  Four monoamine-monoamide dithiol (MAMA) ligands containing two or one nitroimidazole moieties were synthesized and labeled with Tc-99m (labeling yield > 95%). The proposed structures of Tc-99m-complexes are identified by comparison with analogous Re-MAMA complexes. Tc-99m-MAMA complexes show better physicochemical characters than (TcO)-Tc-99m-(PnAO-1-(2-nitroimidazole)). Reduction potentials of nitro groups of the rhenium complexes are within the range for bioreductive compounds. As expected, biodistribution studies demonstrate that the 2-nitroimidazole complex shows better tumor-to-tissue ratios than 4-nitroimidazole analog for mononitroimidazole complexes, but not for MAMA-bisnitroimidazoles due to higher lipophilicity. Both the bisnitroimidazole compounds show rapider excretion, lower background activity in liver and higher tumor-to-tissue ratios than the mono-nitroimidazoles. Better biodistribution characteristic makes both the MAMA-bisnitroimidazole complexes, especially (TC)-T-99m-15, be potential tumor hypoxia marker. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.042