3-((4-(4-methoxyphenyl)piperazin-1-yl)methyl)-1H-indole | 864389-09-3

• 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-methoxyphenyl)piperazin-1-yl)methyl)-1H-indole
• 英文别名: 3-{[4-(4-methoxyphenyl)-1-piperazinyl]methyl}-1H-indole；3-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-1H-indole
• CAS: 864389-09-3
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: CRJJXHKBVLJRSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  31.5
• 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-甲氧基苯基)哌嗪 以 乙醇 、 水 为溶剂， 以22%的产率得到3-((4-(4-methoxyphenyl)piperazin-1-yl)methyl)-1H-indole
  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

• 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。
• Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida, Journal of the Chemical Society of Pakistan, 2012, vol. 34, # 3, p. 748 - 757
  作者：Khan, Khalid Mohammed、Rahim, Fazal、Ambreen, Nida、Taha, Muhammad、Iqbal, Sarosh、Haider, Syed Moazzam、Perveen, Shahnaz

  DOI：——

  日期：——
• Synthetic indole Mannich bases: Their ability to modulate in vitro cellular immunity
  作者：M. Ahmed Mesaik、Khalid Mohammed Khan、Fazal Rahim、Muhammad Taha、Syed Moazzam Haider、Shahnaz Perveen、Ahmed Shukralla Khalid、Omer M. Abdalla、Samreen Soomro、Wolfgang Voelter

  DOI：10.1016/j.bioorg.2015.05.003

  日期：2015.6

  The synthetic indole Mannich bases 1-13 have been investigated for their ability to modulate immune responses measured in vitro. These activities were based on monitoring their affects on T-lymphocyte proliferation, reactive oxygen species (ROS), IL (interleukin)-2, IL-4, and nitric oxide production. Compound 5 was found to be the most potent immunomodulator in this context. Four of the synthesized compounds, 5, 11, 12, and 13, have significant potent inhibitory effects on T-cell proliferation, IL-4, and nitric oxide production. However, none of the thirteen indole compounds exerted any activity against ROS production. (C) 2015 Elsevier Inc. All rights reserved.