[18F]-1-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-4-((2-(2-(2-nitro-1H-imidazol-1-yl)ethoxy)ethoxy)methyl)-1H-1,2,3-triazole | 1443039-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [18F]-1-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-4-((2-(2-(2-nitro-1H-imidazol-1-yl)ethoxy)ethoxy)methyl)-1H-1,2,3-triazole
• 英文别名: (18F)fluoranyl-dinaphthalen-1-yl-[3-[4-[2-[2-(2-nitroimidazol-1-yl)ethoxy]ethoxymethyl]triazol-1-yl]propyl]silane
• CAS: 1443039-69-7
• 化学式: C₃₃H₃₃FN₆O₄Si
• 分子量: 623.748
• InChiKey: XBKTYJCNYFLAOD-JNPIJYQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-(2-(2-chloroethoxy)ethoxy)prop-1-yne 在 copper(ll) sulfate pentahydrate 、 [¹⁸F]fluoride 、 sodium ascorbate 、 potassium carbonate 、 溶剂黄146 、 sodium iodide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 [18F]-1-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-4-((2-(2-(2-nitro-1H-imidazol-1-yl)ethoxy)ethoxy)methyl)-1H-1,2,3-triazole
  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.