N-(5-bromo-2-phenoxyphenyl)acetamide | 928637-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(5-bromo-2-phenoxyphenyl)acetamide
• CAS: 928637-39-2
• 化学式: C₁₄H₁₂BrNO₂
• 分子量: 306.159
• InChiKey: WMYJHYYXUIUOBA-UHFFFAOYSA-N

物化性质

• 沸点：
  418.7±35.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-2-phenoxyphenyl)acetamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.0h， 生成 N-­(2,5-dimethoxybenzyl)-N-­(2-­phenoxy-­5-(4,4,5,5-tetramethyl-1,3,2-­dioxaborolan-2-yl)phenyl)acetamide
  参考文献：
  名称：

  Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications

  摘要：

  使用铜介导的非载体添加亲核性¹⁸F-氟化技术，从芳基硼酸酯前体中分离出了八种临床相关的放射性示踪剂。

  DOI：

  10.1039/c6cc03295h
• 作为产物：
  描述：

  4-溴-2-硝基-1-苯氧基苯 在 铁粉 、 氯化铵 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 N-(5-bromo-2-phenoxyphenyl)acetamide
  参考文献：
  名称：

  Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications

  摘要：

  使用铜介导的非载体添加亲核性¹⁸F-氟化技术，从芳基硼酸酯前体中分离出了八种临床相关的放射性示踪剂。

  DOI：

  10.1039/c6cc03295h

文献信息

• <i>N</i>-(5-Fluoro-2-phenoxyphenyl)-<i>N</i>-(2-[¹³¹I]iodo-5-methoxybenzyl)acetamide:  A Potent Iodinated Radioligand for the Peripheral-type Benzodiazepine Receptor in Brain
  作者：Ming-Rong Zhang、Katsushi Kumata、Jun Maeda、Terushi Haradahira、Junko Noguchi、Tetsuya Suhara、Christer Halldin、Kazutoshi Suzuki

  DOI：10.1021/jm061127n

  日期：2007.2.1

  To image the peripheral-type benzodiazepine receptor (PBR) in vivo, we previously developed two positron emission tomography (PET) ligands, N-(2-[C-11],5-dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)acetamide ([C-11]1a) and its [F-18]fluoroethyl analogue ([F-18]1b), for the investigation of PBR in the living human brain. This time, using 1a as a leading compound, we designed two novel iodinated analogues, N-(5-fluoro-2-phenoxyphenyl)-N-(2-iodo-5-methoxybenzyl)acetamide (3a) and N-(2,5-dimethoxybenzyl)-N-(5-iodo-2-phenoxyphenyl)acetamide (3b) for the PBR imaging. Ligands 3 were synthesized by the iodination of tributystannyl precursors 10. Radiolabeling for 3 with I-131 was carried out by the reaction of 10 with [I-131]NaI using H2O2 as an oxidizing agent. In vitro competition experiments determined that 3a exhibited both high affinity and selectivity for PBR (IC50: 7.8 nM) vs CBR (> 1 mu M). Biodistribution study in mice determined that [I-131]3a had a high radioactivity level (1.69% dose/g) in the brain, and its distribution pattern in the brain was consistent with the known distribution of PBR in rodents. Ex vivo autoradiography of the rat brain gave visual evidence that [I-131]3a was a potent and specific radioligand for PBR.