1-[1-(4-bromobutyl)indol-5-yl]-ethanone | 1340592-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[1-(4-bromobutyl)indol-5-yl]-ethanone
• CAS: 1340592-90-6
• 化学式: C₁₄H₁₆BrNO
• 分子量: 294.191
• InChiKey: JMZBFJSISYIZPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-环己基哌嗪 、 1-[1-(4-bromobutyl)indol-5-yl]-ethanone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-{1-[4-(4-cyclohexyl-piperazin-1-yl)-butyl]indol-5-yl}-ethanone
  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
• 作为产物：
  描述：

  1,4-二溴丁烷 、 5-乙酰吲哚 在 四丁基碘化铵 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以67%的产率得到1-[1-(4-bromobutyl)indol-5-yl]-ethanone
  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