(2S)-N-(3-aminopropyl)-2,6-bis[3-(4-nitroimidazol-1-yl)propanoylamino]hexanamide | 1416134-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-N-(3-aminopropyl)-2,6-bis[3-(4-nitroimidazol-1-yl)propanoylamino]hexanamide
• CAS: 1416134-21-8
• 化学式: C₂₁H₃₂N₁₀O₇
• 分子量: 536.548
• InChiKey: MNSSTWRYSVVRBU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  241
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  、 (2S)-N-(3-aminopropyl)-2,6-bis[3-(4-nitroimidazol-1-yl)propanoylamino]hexanamide 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以70.8%的产率得到
  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
• 作为产物：
  描述：

  methyl 2,6-diacrylamidohexanoate 以 甲醇 、 三乙胺 为溶剂， 反应 208.0h， 生成 (2S)-N-(3-aminopropyl)-2,6-bis[3-(4-nitroimidazol-1-yl)propanoylamino]hexanamide
  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

文献信息

• 99mTc/Re complexes bearing bisnitroimidazole or mononitroimidazole as potential bioreductive markers for tumor: Synthesis, physicochemical characterization and biological evaluation
  作者：Lei Mei、Yue Wang、Taiwei Chu

  DOI：10.1016/j.ejmech.2012.09.042

  日期：2012.12

  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.