1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole | 1345510-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole
• 英文别名: 1-{3-[4-(substitutedphenyl)piperazin1-yl]propyl}-1 H-indole, 4a；1-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]indole
• CAS: 1345510-84-0
• 化学式: C₂₁H₂₄FN₃
• 分子量: 337.44
• InChiKey: ROSNMWHSNPNNNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  11.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole
  参考文献：
  名称：

  Synthesis and in vitro Evaluation of Novel Indole-Based Sigma Receptors Ligands

  摘要：

  To investigate the molecular features involved in sigma (σ) receptors binding, a series of compounds based on indole scaffolds were synthesized and their chemical structures were confirmed by 1H‐NMR, IR, and elemental analysis. Their affinity toward σ1 and σ2 receptor subtypes was evaluated. 1‐{[4‐(2‐phenylethyl)piperazin‐1‐yl]methyl}‐3‐methyl‐1H‐indole 3b had a high affinity to σ1 receptors, while three compounds, 1‐{3‐[4‐(substitutedphenyl)piperazin‐1‐yl]propyl}‐1H‐indole derivatives 4a–c had shown high affinity and selectivity for σ2 receptors. Cytotoxicity of the compounds was demonstrated on cancer cell lines from liver (HUH7), breast (MCF7), and colon (HCT‐116) cancer cell lines. Compound 1c (3‐{[4‐(3,4‐dichlorobenzyl)piperazin‐1‐yl]methyl}‐1H‐indole) showed significant cell growth inhibitory activity on the selected cancer cell lines.

  DOI：

  10.1111/j.1747-0285.2011.01215.x

文献信息

• Synthesis and in vitro Evaluation of Novel Indole-Based Sigma Receptors Ligands
  作者：Mine Yarim、Meric Koksal、Dirk Schepmann、Bernard Wünsch

  DOI：10.1111/j.1747-0285.2011.01215.x

  日期：2011.11

  To investigate the molecular features involved in sigma (σ) receptors binding, a series of compounds based on indole scaffolds were synthesized and their chemical structures were confirmed by 1H‐NMR, IR, and elemental analysis. Their affinity toward σ1 and σ2 receptor subtypes was evaluated. 1‐[4‐(2‐phenylethyl)piperazin‐1‐yl]methyl}‐3‐methyl‐1H‐indole 3b had a high affinity to σ1 receptors, while three compounds, 1‐3‐[4‐(substitutedphenyl)piperazin‐1‐yl]propyl}‐1H‐indole derivatives 4a–c had shown high affinity and selectivity for σ2 receptors. Cytotoxicity of the compounds was demonstrated on cancer cell lines from liver (HUH7), breast (MCF7), and colon (HCT‐116) cancer cell lines. Compound 1c (3‐[4‐(3,4‐dichlorobenzyl)piperazin‐1‐yl]methyl}‐1H‐indole) showed significant cell growth inhibitory activity on the selected cancer cell lines.