3-chloro-3-methyl-1-(4-nitro-1H-imidazol-1-yl)butan-2-one oxime | 1356854-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-chloro-3-methyl-1-(4-nitro-1H-imidazol-1-yl)butan-2-one oxime
• CAS: 1356854-36-8
• 化学式: C₈H₁₁ClN₄O₃
• 分子量: 246.653
• InChiKey: SVEIYXQEAIHCTH-UHFFFAOYSA-N

物化性质

• 沸点：
  471.8±35.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-chloro-3-methyl-1-(4-nitro-1H-imidazol-1-yl)butan-2-one oxime 、 1,3-丙二胺 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以64%的产率得到3,3'-(propane-1,3-diylbis(azanediyl))bis(3-methyl-1-(4-nitro-1H-imidazol-1-yl)butan-2-one) dioxime
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.11.042