4-(5-(5-bromopentyloxy)benzo[d]oxazol-2-yl)-N,N-dimethylbenzenamine | 1384435-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-(5-bromopentyloxy)benzo[d]oxazol-2-yl)-N,N-dimethylbenzenamine
• CAS: 1384435-28-2
• 化学式: C₂₀H₂₃BrN₂O₂
• 分子量: 403.319
• InChiKey: PXVKIJGCDJTFSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(5-(5-bromopentyloxy)benzo[d]oxazol-2-yl)-N,N-dimethylbenzenamine 在 三乙基硅烷 、 potassium carbonate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 0.34h， 生成 2-((5-((2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yl)oxy)pentyl)(2-((2-mercaptoethyl)amino)ethyl)amino)ethanethiol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel technetium-99m labeled phenylbenzoxazole derivatives as potential imaging probes for β-amyloid plaques in brain

  摘要：

  Two uncharged Tc-99m-labeled phenylbenzoxazole derivatives were biologically evaluated as potential imaging probes for beta-amyloid plaques. The Tc-99m and corresponding rhenium complexes were synthesized by coupling monoamine-monoamide dithiol (MAMA) and bis(aminoethanethiol) (BAT) chelating ligand via a pentyloxy spacer to phenylbenzoxazole. The fluorescent rhenium complexes 6 and 9 selectively stainined the beta-amyloid plaques on the sections of transgenic mouse, and showed high affinity for A beta((1-42)) aggregates (K-i = 11.1 nM and 14.3 nM, respectively). Autoradiography in vitro indicated that [Tc-99m]6 clearly labeled beta-amyloid plaques on the sections of transgenic mouse. Biodistribution experiments in normal mice revealed that [Tc-99m]6 displayed moderate initial brain uptake (0.81% ID/g at 2 min), and quickly washed out from the brain (0.25% ID/g at 60 min). The preliminary results indicate that the properties of [Tc-99m]6 are promising, although additional refinements are needed to improve the ability to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.010
• 作为产物：
  描述：

  4-(5-methoxybenzo[d]oxazol-2-yl)-N,N-dimethylaniline 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 4-(5-(5-bromopentyloxy)benzo[d]oxazol-2-yl)-N,N-dimethylbenzenamine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel technetium-99m labeled phenylbenzoxazole derivatives as potential imaging probes for β-amyloid plaques in brain

  摘要：

  Two uncharged Tc-99m-labeled phenylbenzoxazole derivatives were biologically evaluated as potential imaging probes for beta-amyloid plaques. The Tc-99m and corresponding rhenium complexes were synthesized by coupling monoamine-monoamide dithiol (MAMA) and bis(aminoethanethiol) (BAT) chelating ligand via a pentyloxy spacer to phenylbenzoxazole. The fluorescent rhenium complexes 6 and 9 selectively stainined the beta-amyloid plaques on the sections of transgenic mouse, and showed high affinity for A beta((1-42)) aggregates (K-i = 11.1 nM and 14.3 nM, respectively). Autoradiography in vitro indicated that [Tc-99m]6 clearly labeled beta-amyloid plaques on the sections of transgenic mouse. Biodistribution experiments in normal mice revealed that [Tc-99m]6 displayed moderate initial brain uptake (0.81% ID/g at 2 min), and quickly washed out from the brain (0.25% ID/g at 60 min). The preliminary results indicate that the properties of [Tc-99m]6 are promising, although additional refinements are needed to improve the ability to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.010