[18F]-2-(2-nitro-imidazol-1-yl)-N-(3,3,3-trifluoropropyl)acetamide

• 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: [18F]-2-(2-nitro-imidazol-1-yl)-N-(3,3,3-trifluoropropyl)acetamide
• 英文别名: [18F]-EF3；[18F]-2-(2-Nitroimidazol-1H-yl)-(3,3,3-trifluoropropyl)acetamide；N-(3-(18F)fluoranyl-3,3-difluoropropyl)-2-(2-nitroimidazol-1-yl)acetamide
• 化学式: C₈H₉F₃N₄O₃
• 分子量: 265.181
• InChiKey: ZMQGRZRWRQFMAN-RVRFMXCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3,5,6-四氟苯基(2-硝基-1H-咪唑-1-基)乙酸酯 、 [18F]-3,3,3-trifluoropropylamine 以 乙腈 为溶剂， 以70%的产率得到[18F]-2-(2-nitro-imidazol-1-yl)-N-(3,3,3-trifluoropropyl)acetamide
  参考文献：
  名称：

  Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia

  摘要：

  [F-18]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([F-18]-EF3) has been prepared, in 65% chemical yield and 5% radiochemical yield, by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate 1 with [F-18]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [F-18]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [F-18]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [F-18]-HF production in the cyclotron to the purification of the final target. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00279-0

文献信息

• Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia
  作者：Olivier Josse、Daniel Labar、Benoit Georges、Vincent Grégoire、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0968-0896(00)00279-0

  日期：2001.3

  [F-18]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([F-18]-EF3) has been prepared, in 65% chemical yield and 5% radiochemical yield, by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate 1 with [F-18]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [F-18]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [F-18]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [F-18]-HF production in the cyclotron to the purification of the final target. (C) 2001 Elsevier Science Ltd. All rights reserved.