7-acetoxy-2-acetyl-1-(4'-chlorophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline | 900804-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 7-acetoxy-2-acetyl-1-(4'-chlorophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 900804-65-1
• 化学式: C₂₀H₂₀ClNO₄
• 分子量: 373.836
• InChiKey: CNNBSUFZEQKROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-acetoxy-2-acetyl-1-(4'-chlorophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以60%的产率得到N-acetyl-1-(4'-chlorophenyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Closing in on the AMPA receptor: Synthesis and evaluation of 2-acetyl-1-(4′-chlorophenyl)-6-methoxy-7-[11C]methoxy-1,2,3,4-tetrahydroisoquinoline as a potential PET tracer

  摘要：

  2-Acetyl-1-(4'-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, one of the most potent non-competitive AMPA antagonists described to date, has been labelled with carbon-11 and tritium and evaluated as a potential ligand for in vivo imaging of AMPA receptors using PET. The carbon-11 labelled compound showed good initial brain uptake in rats, but with rapid clearance and relatively homogenous distribution. In saturation binding studies, the tritiated racemic ligand was found to be highly potent with a K(d) of 14.8 +/- 1.8 nM. We conclude that the low receptor density labelled with this compound, its rapid clearance from the CNS and low specific binding makes it unsuitable as an in vivo PET imaging agent for AMPA receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.034
• 作为产物：
  描述：

  N-(4-chlorobenzylidene)-N-[2-(3'-methoxy-4'-hydroxyphenyl)ethyl]amine 在 三氟乙酸 作用下， 反应 3.0h， 生成 7-acetoxy-2-acetyl-1-(4'-chlorophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Closing in on the AMPA receptor: Synthesis and evaluation of 2-acetyl-1-(4′-chlorophenyl)-6-methoxy-7-[11C]methoxy-1,2,3,4-tetrahydroisoquinoline as a potential PET tracer

  摘要：

  2-Acetyl-1-(4'-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, one of the most potent non-competitive AMPA antagonists described to date, has been labelled with carbon-11 and tritium and evaluated as a potential ligand for in vivo imaging of AMPA receptors using PET. The carbon-11 labelled compound showed good initial brain uptake in rats, but with rapid clearance and relatively homogenous distribution. In saturation binding studies, the tritiated racemic ligand was found to be highly potent with a K(d) of 14.8 +/- 1.8 nM. We conclude that the low receptor density labelled with this compound, its rapid clearance from the CNS and low specific binding makes it unsuitable as an in vivo PET imaging agent for AMPA receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.034