3-<4-(4-Fluorphenyl)piperazinomethyl)indol | 20094-55-7

• 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: 3-<4-(4-Fluorphenyl)piperazinomethyl)indol
• 英文别名: 3-<4-(4-Fluorphenyl)-1-piperazinylmethyl)indol；3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-1H-indole；3-[4-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-indole；3-{[4-(4-fluorophenyl)piperazino]methyl}-1H-indole；3-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-1H-indole
• CAS: 20094-55-7
• 化学式: C₁₉H₂₀FN₃
• 分子量: 309.386
• InChiKey: PCLWAFVRAWUFRN-UHFFFAOYSA-N

物化性质

• 熔点：
  166.8 °C(Solvent: Ethanol; Water)
• 沸点：
  493.283±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  22.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 聚合甲醛 、 1-(4-氟苯基)哌嗪 以 乙醇 、 水 为溶剂， 以63%的产率得到3-<4-(4-Fluorphenyl)piperazinomethyl)indol
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of indole-based 1,4-disubstituted piperazines as cytotoxic agents

  摘要：

  一系列3-[(4-取代哌嗪-1-基)甲基]-1H-吲哚衍生物被合成，并通过光谱分析确认了其结构。所有化合物均在体外针对三种人肿瘤细胞系进行细胞毒性活性测试：人肝（HUH7）、乳腺（MCF7）和结肠（HCT116）。在设计的衍生物中，大多数化合物对肝癌和结肠癌细胞系显示出显著的细胞毒性，其IC_{50}浓度低于标准药物5-氟尿嘧啶。化合物3s，其哌嗪环上具有3,4-二氯苯基取代基，在抑制所有筛选的癌细胞生长方面最为活跃。

  DOI：

  10.3906/kim-1111-5

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.
• US9566284B2
  申请人：——

  公开号：US9566284B2

  公开（公告）日：2017-02-14
• Design, synthesis, and biological evaluation of indole-based 1,4-disubstituted piperazines as cytotoxic agents
  作者：MERİÇ KÖKSAL AKKOÇ、MİNE YARIM YÜKSEL、İREM DURMAZ、RENGÜL ÇETİN ATALAY

  DOI：10.3906/kim-1111-5

  日期：——

  A series of 3-[(4-substitutedpiperazin-1-yl)methyl]-1H-indole derivatives were synthesized, and their structures were confirmed by spectral analysis. All the compounds were tested for their cytotoxic activity in vitro against 3 human tumor cell lines: human liver (HUH7), breast (MCF7), and colon (HCT116). Among the designed derivatives, most of the compounds showed significant cytotoxicity against liver and colon cancer cell lines with lower IC_50} concentrations than the standard drug 5-fluorouracil. Compound 3s, with 3,4-dichlorophenyl substituent on the piperazine ring, was the most active in suppressing the growth of all screened cancer cells.

  一系列3-[(4-取代哌嗪-1-基)甲基]-1H-吲哚衍生物被合成，并通过光谱分析确认了其结构。所有化合物均在体外针对三种人肿瘤细胞系进行细胞毒性活性测试：人肝（HUH7）、乳腺（MCF7）和结肠（HCT116）。在设计的衍生物中，大多数化合物对肝癌和结肠癌细胞系显示出显著的细胞毒性，其IC_50}浓度低于标准药物5-氟尿嘧啶。化合物3s，其哌嗪环上具有3,4-二氯苯基取代基，在抑制所有筛选的癌细胞生长方面最为活跃。