2-(2-(2-((2-(4-(methylamino)phenyl)benzo[d]oxazol-5-yl)oxy)ethoxy)ethoxy)ethanol | 1383563-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-(2-((2-(4-(methylamino)phenyl)benzo[d]oxazol-5-yl)oxy)ethoxy)ethoxy)ethanol
• 英文别名: 2-[2-[2-[[2-[4-(Methylamino)phenyl]-1,3-benzoxazol-5-yl]oxy]ethoxy]ethoxy]ethanol；2-[2-[2-[[2-[4-(methylamino)phenyl]-1,3-benzoxazol-5-yl]oxy]ethoxy]ethoxy]ethanol
• CAS: 1383563-11-8
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: XEZKBVOLHKUIAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  86
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-(2-((2-(4-(methylamino)phenyl)benzo[d]oxazol-5-yl)oxy)ethoxy)ethoxy)ethanol 在 二乙胺基三氟化硫 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以9.6%的产率得到4-(5-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N-methylaniline
  参考文献：
  名称：

  Novel ¹⁸F-Labeled Benzoxazole Derivatives as Potential Positron Emission Tomography Probes for Imaging of Cerebral β-Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Two radiofluoro-pegylated phenylbenzoxazole derivatives, 4-(5-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo-[d]oxazol-2-yl)-N-methylaniline ([F-18]24) and 4-(5-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N,N-dimethylaniline ([F-18]32), were synthesized and evaluated as probes for imaging cerebral beta-amyloid (A beta) plaques in living brain tissue by PET. [F-18]24 and [F-18]32 displayed high affinity for A beta(1-42) aggregates (K-1 = 9.3 and 3.9 nM, respectively). In vitro autoradiography with sections of post-mortem AD brain and transgenic mouse brain confirmed the affinity of these tracers. Initial high uptake into and rapid washout from the brain in normal mice were observed. [F-18]24 also displayed excellent binding to A beta plaques in ex vivo autoradiographic experiments with Tg2576 mice. Furthermore, small-animal PET studies demonstrated significant differences in the clearance profile after the administration of [F-18]24 between Tg2576 and wild-type mice. The results suggest [F-18]24 to be a useful PET agent for detecting A beta plaques in the living human brain.

  DOI：

  10.1021/jm300251n
• 作为产物：
  描述：

  4-甲氧基-2-硝基酚 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 2-(2-(2-((2-(4-(methylamino)phenyl)benzo[d]oxazol-5-yl)oxy)ethoxy)ethoxy)ethanol
  参考文献：
  名称：

  Novel ¹⁸F-Labeled Benzoxazole Derivatives as Potential Positron Emission Tomography Probes for Imaging of Cerebral β-Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Two radiofluoro-pegylated phenylbenzoxazole derivatives, 4-(5-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo-[d]oxazol-2-yl)-N-methylaniline ([F-18]24) and 4-(5-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N,N-dimethylaniline ([F-18]32), were synthesized and evaluated as probes for imaging cerebral beta-amyloid (A beta) plaques in living brain tissue by PET. [F-18]24 and [F-18]32 displayed high affinity for A beta(1-42) aggregates (K-1 = 9.3 and 3.9 nM, respectively). In vitro autoradiography with sections of post-mortem AD brain and transgenic mouse brain confirmed the affinity of these tracers. Initial high uptake into and rapid washout from the brain in normal mice were observed. [F-18]24 also displayed excellent binding to A beta plaques in ex vivo autoradiographic experiments with Tg2576 mice. Furthermore, small-animal PET studies demonstrated significant differences in the clearance profile after the administration of [F-18]24 between Tg2576 and wild-type mice. The results suggest [F-18]24 to be a useful PET agent for detecting A beta plaques in the living human brain.

  DOI：

  10.1021/jm300251n