2-((4-苯氧基吡啶-3-基氨基)甲基)苯酚 | 1005325-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-((4-苯氧基吡啶-3-基氨基)甲基)苯酚
• 英文名称: 2-((4-phenoxypyridin-3-ylamino)methyl)phenol
• 英文别名: 2-[[(4-Phenoxy-3-pyridinyl)amino]methyl]phenol；2-[[(4-phenoxypyridin-3-yl)amino]methyl]phenol
• CAS: 1005325-41-6
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: RFQIRFQBBVAAOI-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C (decomp)
• 沸点：
  465.7±40.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-苯氧基吡啶-3-基氨基)甲基)苯酚 生成 N-(2-hydroxybenzyl)-N-(4-phenoxypyridin-3-yl)acetamide
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2012, 22, 5795-5800

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-((4-苯氧基吡啶-3-基氨基)甲基)苯酚
  参考文献：
  名称：

  Fully automated synthesis and initial PET evaluation of [11C]PBR28

  摘要：

  Fully automated synthesis and initial PET evaluation of a TSPO radioligand, [C-11]PBR28 (N-(2[C-11]methoxybenzyl)-N-(4-phenoxypyridin-3-yl)acetamide), are reported. These results facilitate the potential preclinical and clinical PET studies of [C-11]PBR28 in animals and humans. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.051

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.
• A novel one-pot palladium-mediated synthesis of N-[(2-hydroxyphenyl)methyl]-N-(4-phenoxy-3-pyridinyl) acetamide, the precursor to [11C]PBR28, a PET biomarker for the peripheral benzodiazepine receptor
  作者：Raphaël Hoareau、Peter J.H. Scott

  DOI：10.1016/j.tetlet.2010.04.089

  日期：2010.6

  Due to an urgent need to image the peripheral benzodiazepine receptor (PBR) in living human subjects using positron emission tomography imaging, we had cause to prepare N-[(2-hydroxyphenyl)methyl]-N-(4-phenoxy-3-pyridinyl) acetamide (desmethyl-PBR28 (1)), the precursor to [C-11]PBR28. Herein, we report a new synthesis of the precursor in which palladium-mediated reduction of the nitro pyridine to the corresponding amino pyridine, and subsequent reductive amination, can be achieved with decaborane in a convenient one-pot procedure. This procedure is operationally simpler than the current alternatives and provides high quality precursor suitable for use in clinical applications. (C) 2010 Elsevier Ltd. All rights reserved.
• J. Med. Chem. 2008, 51, 17-30
  作者：

  DOI：——

  日期：——
• Fully automated synthesis and initial PET evaluation of [11C]PBR28
  作者：Min Wang、Karmen K. Yoder、Mingzhang Gao、Bruce H. Mock、Xiao-Ming Xu、Andrew J. Saykin、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2009.08.051

  日期：2009.10

  Fully automated synthesis and initial PET evaluation of a TSPO radioligand, [C-11]PBR28 (N-(2[C-11]methoxybenzyl)-N-(4-phenoxypyridin-3-yl)acetamide), are reported. These results facilitate the potential preclinical and clinical PET studies of [C-11]PBR28 in animals and humans. (C) 2009 Elsevier Ltd. All rights reserved.
• Bioorg. Med. Chem. Lett. 2012, 22, 5795-5800
  作者：

  DOI：——

  日期：——