6-[18F]fluoro-PBR28 | 1330574-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[18F]fluoro-PBR28
• 英文别名: N-(6-fluoro-4-phenoxypyridin-3-yl)-N-(2-methoxybenzyl)acetamide；N-(6-(18F)fluoranyl-4-phenoxypyridin-3-yl)-N-[(2-methoxyphenyl)methyl]acetamide
• CAS: 1330574-90-7
• 化学式: C₂₁H₁₉FN₂O₃
• 分子量: 365.393
• InChiKey: AWEYHVLPBGXFIH-KVTPGWOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-nitro-4-phenoxypyridin-2-ol 在 铁粉 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 、 二甲基亚砜 、 甲苯 为溶剂， 反应 0.08h， 生成 6-[18F]fluoro-PBR28
  参考文献：
  名称：

  Synthesis of 6-[18F]fluoro-PBR28, a novel radiotracer for imaging the TSPO 18kDa with PET

  摘要：

  6-Fluoro-PBR28 (N-(6-fluoro-4-phenoxypyridin-3-yl)-N-(2-methoxybenzyl) acetamide), a fluorinated analogue of the recently developed TSPO 18 kDa ligand PBR28, was synthesized and labelled with fluorine- 18. 6-Fluoro-PBR28 and its 6-chloro/6-bromo counterparts were synthesized in six chemical steps and obtained in 16%, 10% and 19% overall yields, respectively. Labelling with fluorine-18 was performed in one single step (chlorine/bromine-for-fluorine heteroaromatic substitution) using a Zymate-XP robotic system affording HPLC-purified, ready-to-inject, 6-[F-18] fluoro-PBR28 (> 95% radiochemically pure). Non-decay-corrected overall yields were 9-10% and specific radioactivities ranged from 74 to 148 GBq/mu mol. In vitro binding experiments, dynamic mu PET studies performed in a rat model of acute neuroinflammation (unilaterally, AMPA-induced, striatum-lesioned rats) and ex vivo autoradiography on the same model demonstrated the potential of 6-[F-18] fluoro-PBR28 to image the TSPO 18 kDa using PET. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.048

文献信息

• Synthesis of 6-[18F]fluoro-PBR28, a novel radiotracer for imaging the TSPO 18kDa with PET
  作者：Annelaure Damont、Raphaël Boisgard、Bertrand Kuhnast、Frédéric Lemée、Guillaume Raggiri、Alana M. Scarf、Eleonora Da Pozzo、Silvia Selleri、Claudia Martini、Bertrand Tavitian、Michael Kassiou、Frédéric Dollé

  DOI：10.1016/j.bmcl.2011.06.048

  日期：2011.8

  6-Fluoro-PBR28 (N-(6-fluoro-4-phenoxypyridin-3-yl)-N-(2-methoxybenzyl) acetamide), a fluorinated analogue of the recently developed TSPO 18 kDa ligand PBR28, was synthesized and labelled with fluorine- 18. 6-Fluoro-PBR28 and its 6-chloro/6-bromo counterparts were synthesized in six chemical steps and obtained in 16%, 10% and 19% overall yields, respectively. Labelling with fluorine-18 was performed in one single step (chlorine/bromine-for-fluorine heteroaromatic substitution) using a Zymate-XP robotic system affording HPLC-purified, ready-to-inject, 6-[F-18] fluoro-PBR28 (> 95% radiochemically pure). Non-decay-corrected overall yields were 9-10% and specific radioactivities ranged from 74 to 148 GBq/mu mol. In vitro binding experiments, dynamic mu PET studies performed in a rat model of acute neuroinflammation (unilaterally, AMPA-induced, striatum-lesioned rats) and ex vivo autoradiography on the same model demonstrated the potential of 6-[F-18] fluoro-PBR28 to image the TSPO 18 kDa using PET. (C) 2011 Elsevier Ltd. All rights reserved.