2-(4-(3-(furan-3-yl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 1340593-09-0

• 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: 2-(4-(3-(furan-3-yl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-[4-[3-(furan-3-yl)indol-1-yl]butyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
• CAS: 1340593-09-0
• 化学式: C₂₇H₃₀N₂O₃
• 分子量: 430.547
• InChiKey: HDPQGGCUKVMKGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(furan-3-yl)-1-(phenylsulfonyl)-1H-indole 在 甲醇 、 四丁基碘化铵 、 potassium carbonate 、 氯化铵 、 magnesium 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-(4-(3-(furan-3-yl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of indole-based sigma receptor ligands

  摘要：

  A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant selectivity over sigma-1 receptors. In particular, 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9f) was found to display high affinity at sigma-2 receptors with good selectivity (sigma-1/sigma-2 = 395). The pharmacological binding profile for this compound was established with other relevant non-sigma sites. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.031

文献信息

• Synthesis and pharmacological evaluation of indole-based sigma receptor ligands
  作者：Christophe Mésangeau、Emanuele Amata、Walid Alsharif、Michael J. Seminerio、Matthew J. Robson、Rae R. Matsumoto、Jacques H. Poupaert、Christopher R. McCurdy

  DOI：10.1016/j.ejmech.2011.08.031

  日期：2011.10

  A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant selectivity over sigma-1 receptors. In particular, 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9f) was found to display high affinity at sigma-2 receptors with good selectivity (sigma-1/sigma-2 = 395). The pharmacological binding profile for this compound was established with other relevant non-sigma sites. (C) 2011 Elsevier Masson SAS. All rights reserved.