N-(2-fluoroethyl)-3-methoxyaniline | 1360061-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(2-fluoroethyl)-3-methoxyaniline
• CAS: 1360061-00-2
• 化学式: C₉H₁₂FNO
• 分子量: 169.199
• InChiKey: IMOJEUYMSZFVJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-fluoroethyl)-3-methoxyaniline 在 草酰氯 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 9-(2-fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride
  参考文献：
  名称：

  [18F]GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18kDa (TSPO)

  摘要：

  A series of tricyclic compounds have been synthesised and evaluated in vitro for affinity against Translocator protein 18 kDa (TSPO) and for preferred imaging properties. The most promising of the compounds were radiolabelled and evaluated in vivo to determine biodistribution and specificity for high expressing TSPO regions. Metabolite profiling in brain and plasma was also investigated. Evaluation in an autoradiography model of neuroinflammation was also carried out for the best compound, 12a ([F-18]GE-180). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.084
• 作为产物：
  描述：

  对甲苯磺酸氟乙酯 、 间氨基苯甲醚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-fluoroethyl)-3-methoxyaniline
  参考文献：
  名称：

  [18F]GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18kDa (TSPO)

  摘要：

  A series of tricyclic compounds have been synthesised and evaluated in vitro for affinity against Translocator protein 18 kDa (TSPO) and for preferred imaging properties. The most promising of the compounds were radiolabelled and evaluated in vivo to determine biodistribution and specificity for high expressing TSPO regions. Metabolite profiling in brain and plasma was also investigated. Evaluation in an autoradiography model of neuroinflammation was also carried out for the best compound, 12a ([F-18]GE-180). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.084

文献信息

• An improved, regioselective synthesis of the radiolabelling precursor for the translocator protein targeting positron emission tomography imaging radiotracer [18F]GE-180
  作者：Véronique Morisson-Iveson、Harry Wadsworth、Joanna Passmore、Amanda Ewan、Sondre Nilsen、Mikkel Thaning、William Trigg

  DOI：10.1016/j.tetlet.2014.07.090

  日期：2014.9

  [18F]GE-180 has been demonstrated to be a promising new positron emission tomography radiotracer for targeting translocator protein. PET imaging of TSPO will enable measurement of neuroinflammation and microglia activity in vivo. The synthetic route used in the initial discovery of GE-180, whilst enabling the rapid evaluation of the structure–activity relationships (SAR) in this molecular class, was

  [ 18 F] GE-180已被证明是有针对性的新型正电子发射断层扫描放射示踪剂，可靶向易位蛋白。TSPO的PET成像将能够测量体内的神经炎症和小胶质细胞活性。GE-180的最初发现中使用的合成途径，尽管能够快速评估该分子类别中的结构-活性关系（SAR），但收率不高，也不适合大规模生产。在这里，我们提出了一条通向GE-180和[ 18 F] GE-180的放射性标记前体的优化路线，其得益于提高合成关键吲哚形成步骤的区域选择性的策略，从而显着提高了收率。