N-(4-phenoxypyridin-3-yl)acetamide | 1005325-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-phenoxypyridin-3-yl)acetamide
• CAS: 1005325-40-5
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: HPPWYOFEHGLYGU-UHFFFAOYSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  401.2±30.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-phenoxypyridin-3-yl)acetamide 、 邻甲氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 25.0h， 以90%的产率得到3-(2-甲氧基苄氨基)-4-苯氧基吡啶
  参考文献：
  名称：

  Synthesis and Evaluation in Monkey of Two Sensitive ¹¹C-Labeled Aryloxyanilide Ligands for Imaging Brain Peripheral Benzodiazepine Receptors In Vivo

  摘要：

  We sought to develop C-11-labeled ligands for sensitive imaging of brain peripheral benzodiazepine receptors (PBR) in vivo. Two aryloxyanilides with high affinity for PBR were identified and synthesized, namely, N-acetyl-N-(2-methoxycarbonylbenzyl)-2-phenoxyaniline (3, PBR01) and N-(2-methoxybenzyI)-N-(4-phenoxypyridin-3-yl)acetamide (10, PBR28). 3 was hydrolyzed to 4, which was esterified with [C-11]iodomethane to provide [C-11]3. The O-desmethyl analogue of 10 was converted into [C-11]10 with [C-11]iodomethane. [C-11]3 and [C-11]10 were each injected into monkey to assess their brain kinetics with positron emission tomography (PET). After administration of either radioligand there was moderately high brain uptake of radioactivity. Receptor blocking and displacement experiments showed that a high proportion of this radioactivity was bound specifically to PBR. In monkey and rat, 3 and 10 were rapidly metabolized by ester hydrolysis and N-debenzylation, respectively, each to a single polar radiometabolite. [C-11]3 and [C-11]10 are effective for imaging PBR in monkey brain. [C-11]10 especially warrants further evaluation in human subjects.

  DOI：

  10.1021/jm0707370
• 作为产物：
  描述：

  4-phenoxypyridin-3-amine 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以55%的产率得到N-(4-phenoxypyridin-3-yl)acetamide
  参考文献：
  名称：

  Synthesis and Evaluation in Monkey of Two Sensitive ¹¹C-Labeled Aryloxyanilide Ligands for Imaging Brain Peripheral Benzodiazepine Receptors In Vivo

  摘要：

  We sought to develop C-11-labeled ligands for sensitive imaging of brain peripheral benzodiazepine receptors (PBR) in vivo. Two aryloxyanilides with high affinity for PBR were identified and synthesized, namely, N-acetyl-N-(2-methoxycarbonylbenzyl)-2-phenoxyaniline (3, PBR01) and N-(2-methoxybenzyI)-N-(4-phenoxypyridin-3-yl)acetamide (10, PBR28). 3 was hydrolyzed to 4, which was esterified with [C-11]iodomethane to provide [C-11]3. The O-desmethyl analogue of 10 was converted into [C-11]10 with [C-11]iodomethane. [C-11]3 and [C-11]10 were each injected into monkey to assess their brain kinetics with positron emission tomography (PET). After administration of either radioligand there was moderately high brain uptake of radioactivity. Receptor blocking and displacement experiments showed that a high proportion of this radioactivity was bound specifically to PBR. In monkey and rat, 3 and 10 were rapidly metabolized by ester hydrolysis and N-debenzylation, respectively, each to a single polar radiometabolite. [C-11]3 and [C-11]10 are effective for imaging PBR in monkey brain. [C-11]10 especially warrants further evaluation in human subjects.

  DOI：

  10.1021/jm0707370

文献信息

• Synthesis and Evaluation in Monkey of Two Sensitive ¹¹C-Labeled Aryloxyanilide Ligands for Imaging Brain Peripheral Benzodiazepine Receptors In Vivo
  作者：Emmanuelle Briard、Sami S. Zoghbi、Masao Imaizumi、Jonathan P. Gourley、H. Umesha Shetty、Jinsoo Hong、Vanessa Cropley、Masahiro Fujita、Robert B. Innis、Victor W. Pike

  DOI：10.1021/jm0707370

  日期：2008.1.1

  We sought to develop C-11-labeled ligands for sensitive imaging of brain peripheral benzodiazepine receptors (PBR) in vivo. Two aryloxyanilides with high affinity for PBR were identified and synthesized, namely, N-acetyl-N-(2-methoxycarbonylbenzyl)-2-phenoxyaniline (3, PBR01) and N-(2-methoxybenzyI)-N-(4-phenoxypyridin-3-yl)acetamide (10, PBR28). 3 was hydrolyzed to 4, which was esterified with [C-11]iodomethane to provide [C-11]3. The O-desmethyl analogue of 10 was converted into [C-11]10 with [C-11]iodomethane. [C-11]3 and [C-11]10 were each injected into monkey to assess their brain kinetics with positron emission tomography (PET). After administration of either radioligand there was moderately high brain uptake of radioactivity. Receptor blocking and displacement experiments showed that a high proportion of this radioactivity was bound specifically to PBR. In monkey and rat, 3 and 10 were rapidly metabolized by ester hydrolysis and N-debenzylation, respectively, each to a single polar radiometabolite. [C-11]3 and [C-11]10 are effective for imaging PBR in monkey brain. [C-11]10 especially warrants further evaluation in human subjects.