N-(2-(4-methoxybenzylthio)ethyl)-2-((2-(4-methoxybenzylthio)ethyl)(5-(2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yloxy)pentyl)amino)acetamide | 1384435-32-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-(4-methoxybenzylthio)ethyl)-2-((2-(4-methoxybenzylthio)ethyl)(5-(2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yloxy)pentyl)amino)acetamide
• CAS: 1384435-32-8
• 化学式: C₄₂H₅₂N₄O₅S₂
• 分子量: 757.031
• InChiKey: LYVSEMGEFOCUSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  53.0
• 可旋转键数：
  23.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(2-(4-methoxybenzylthio)ethyl)-2-((2-(4-methoxybenzylthio)ethyl)(5-(2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yloxy)pentyl)amino)acetamide 在 甲烷磺酸 、 苯甲醚 、 三氟乙酸 作用下， 反应 1.0h， 以49.3%的产率得到tert-butyl 2-((5-(2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yloxy)pentyl)(2-mercaptoethyl)amino)-N-(2-mercaptoethyl)acetamide
  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：

  4-二甲氨基苯甲酸 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 左旋去甲麻黄碱 、 乙腈 为溶剂， 反应 3.5h， 生成 N-(2-(4-methoxybenzylthio)ethyl)-2-((2-(4-methoxybenzylthio)ethyl)(5-(2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yloxy)pentyl)amino)acetamide
  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