N-[3-[3-[[3-hydroxyimino-2-methyl-4-(2-nitroimidazol-1-yl)butan-2-yl]amino]propylamino]-3-methyl-1-(2-nitroimidazol-1-yl)butan-2-ylidene]hydroxylamine | 149877-04-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-[3-[3-[[3-hydroxyimino-2-methyl-4-(2-nitroimidazol-1-yl)butan-2-yl]amino]propylamino]-3-methyl-1-(2-nitroimidazol-1-yl)butan-2-ylidene]hydroxylamine
• CAS: 149877-04-3
• 化学式: C₁₉H₃₀N₁₀O₆
• 分子量: 494.511
• InChiKey: PDFJNQHXOUELPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  217
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[3-[3-[[3-hydroxyimino-2-methyl-4-(2-nitroimidazol-1-yl)butan-2-yl]amino]propylamino]-3-methyl-1-(2-nitroimidazol-1-yl)butan-2-ylidene]hydroxylamine 、 copper dichloride 以 aq. acetate buffer 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Synthesis and radiolabeling of 64Cu-labeled 2-nitroimidazole derivative 64Cu-BMS2P2 for hypoxia imaging

  摘要：

  The objective of this study was to develop a positron emission tomography (PET) probe with hypoxia targeting specificity and a relatively long half-life. The synthesis, Cu-64-labeling in vitro and in vivo study of the novel 2-nitroimidazole complex Cu-64-BMS2P2 is presented in this study. The hypoxia targeting capacity of Cu-64-BMS2P2 in vitro was evaluated and compared with the Cu-64-BMS181321, and confirmed by PET imaging in vivo and immunohistochemistry for carbonic anhydrase 9 (CA9) in a tumor mouse model. These results suggest that Cu-64-BMS2P2 is a promising candidate for PET hypoxia imaging and worthy of further investigations in dynamic hypoxia imaging. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.077
• 作为产物：
  描述：

  1-(3-甲基丁-2-烯基)-2-硝基咪唑 在 盐酸 作用下， 以 乙腈 为溶剂， 生成 N-[3-[3-[[3-hydroxyimino-2-methyl-4-(2-nitroimidazol-1-yl)butan-2-yl]amino]propylamino]-3-methyl-1-(2-nitroimidazol-1-yl)butan-2-ylidene]hydroxylamine
  参考文献：
  名称：

  Synthesis and radiolabeling of 64Cu-labeled 2-nitroimidazole derivative 64Cu-BMS2P2 for hypoxia imaging

  摘要：

  The objective of this study was to develop a positron emission tomography (PET) probe with hypoxia targeting specificity and a relatively long half-life. The synthesis, Cu-64-labeling in vitro and in vivo study of the novel 2-nitroimidazole complex Cu-64-BMS2P2 is presented in this study. The hypoxia targeting capacity of Cu-64-BMS2P2 in vitro was evaluated and compared with the Cu-64-BMS181321, and confirmed by PET imaging in vivo and immunohistochemistry for carbonic anhydrase 9 (CA9) in a tumor mouse model. These results suggest that Cu-64-BMS2P2 is a promising candidate for PET hypoxia imaging and worthy of further investigations in dynamic hypoxia imaging. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.077

文献信息

• Effect of a second nitroimidazole redox centre on the accumulation of a hypoxia marker: Synthesis and in vitro evaluation of 99mTc-labeled bisnitroimidazole propylene amine oxime complexes
  作者：Huafan Huang、Hao Zhou、Zejun Li、Xiangyun Wang、Taiwei Chu

  DOI：10.1016/j.bmcl.2011.11.042

  日期：2012.1

  Up to now, most of the hypoxia markers contain only one nitroimidazole redox centre, such as Oxo[[3,3,9,9-tetramethyl-1-(2-nitro-1H-imidazol-1-yl)-4,8-diazaundecane-2,10-dione dioximato] (3-)-N, N', N '', N''']technetium (Tc-99m-1, BMS181321). Introducing a second nitroimidazole redox centre may enhance the hypoxic accumulation of the markers. In the present work, four Tc-99m-1 (BMS181321, containing one 2-nitroimidazole) analogues, that is, Tc-99m-2 (containing two 2-nitroimidazoles), Tc-99m-3 (containing one 4-nitroimidazole), Tc-99m-4 (containing two 4-nitroimidazoles) and Tc-99m-5 (containing both a 2-nitroimidazole and a 4-nitroimidazole) were synthesized, and the hypoxic accumulation was evaluated in vitro using murine sarcoma S180 cells. Tc-99m-3 and Tc-99m-4 displayed no significant anoxic/normoxic differentials, whereas Tc-99m-1 (BMS181321), Tc-99m-2 and Tc-99m-5 showed high anoxic cellular uptakes. The anoxic uptake of Tc-99m-2 reached up to 59.0 +/- 0.9% at 4 h, which was 2.4 times as that of Tc-99m-1. Tc-99m-2 displayed high hypoxic accumulation, indicating that introducing a second nitroimidazole redox centre, that is, 2-nitroimidazole, affected the hypoxic accumulation. Consequently, Tc-99m-2 may serve as a viable candidate for hypoxia marker. This finding may eventually lead to the development of compounds containing multi-redox centres as hypoxia markers. (C) 2011 Elsevier Ltd. All rights reserved.