[18F]-N-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide | 1443039-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [18F]-N-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide
• 英文别名: N-[3-[fluoranyl(dinaphthalen-1-yl)silyl]propyl]-2-(2-nitroimidazol-1-yl)acetamide
• CAS: 1443039-66-4
• 化学式: C₂₈H₂₅FN₄O₃Si
• 分子量: 511.617
• InChiKey: DMTKGOPBPIAMPT-GBHUPVCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(2-nitro-1H-imidazol-1-yl)acetate 在 [¹⁸F]fluoride 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 [18F]-N-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide
  参考文献：
  名称：

  Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds

  摘要：

  The syntheses of new nitroimidazole compounds using silicon-[F-18]fluorine chemistry for the potential detection of tumor hypoxia are described. [F-18]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/mu mol, however these compounds ([F-18]7 and [F-18]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/mu mol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/mu mol. The labeled compound [F-18]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [F-18]18 is suitable for further in vivo assessments. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.029

文献信息

• Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds
  作者：Yoann Joyard、Rabah Azzouz、Laurent Bischoff、Cyril Papamicaël、Daniel Labar、Anne Bol、Vanessa Bol、Pierre Vera、Vincent Grégoire、Vincent Levacher、Pierre Bohn

  DOI：10.1016/j.bmc.2013.04.029

  日期：2013.7

  The syntheses of new nitroimidazole compounds using silicon-[F-18]fluorine chemistry for the potential detection of tumor hypoxia are described. [F-18]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/mu mol, however these compounds ([F-18]7 and [F-18]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/mu mol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/mu mol. The labeled compound [F-18]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [F-18]18 is suitable for further in vivo assessments. (C) 2013 Elsevier Ltd. All rights reserved.