3-(2-甲氧基苄氨基)-4-苯氧基吡啶 | 253307-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2-甲氧基苄氨基)-4-苯氧基吡啶
• 英文名称: N-(2-methoxybenzyl)-4-phenoxypyridin-3-amine
• 英文别名: 3-(2-Methoxybenzylamino)-4-phenoxy-pyridine；N-[(2-methoxyphenyl)methyl]-4-phenoxypyridin-3-amine
• CAS: 253307-66-3
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: YWVGMYNAOSNGEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-(2-甲氧基苄氨基)-4-苯氧基吡啶 、 氟代乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-fluoro-N-[(2-methoxyphenyl)methyl]-N-(4-phenoxypyridin-3-yl)acetamide
  参考文献：
  名称：

  Exploration of the structure–activity relationship of the diaryl anilide class of ligands for translocator protein—potential novel positron emitting tomography imaging agents

  摘要：

  A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.093
• 作为产物：
  描述：

  3-nitro-4-phenoxypyridine 在 sodium tetrahydroborate 、 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-(2-甲氧基苄氨基)-4-苯氧基吡啶
  参考文献：
  名称：

  Exploration of the structure–activity relationship of the diaryl anilide class of ligands for translocator protein—potential novel positron emitting tomography imaging agents

  摘要：

  A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.093

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.
• 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.
• Exploration of the structure–activity relationship of the diaryl anilide class of ligands for translocator protein—potential novel positron emitting tomography imaging agents
  作者：Harry Wadsworth、Paul A. Jones、Wai-Fung Chau、Clare Durrant、Véronique Morisson-Iveson、Joanna Passmore、Dennis O’Shea、Duncan Wynn、Imtiaz Khan、Andrew Black、Michelle Avory、William Trigg

  DOI：10.1016/j.bmcl.2012.07.093

  日期：2012.9

  A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents. (C) 2012 Elsevier Ltd. All rights reserved.