N-((4-chlorophenyl)(1-methyl-1H-indol-3-yl)methyl)-N-methylbenzenamine | 1314029-52-1

• 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: N-((4-chlorophenyl)(1-methyl-1H-indol-3-yl)methyl)-N-methylbenzenamine
• 英文别名: N-[(4-chlorophenyl)-(1-methylindol-3-yl)methyl]-N-methylaniline
• CAS: 1314029-52-1
• 化学式: C₂₃H₂₁ClN₂
• 分子量: 360.886
• InChiKey: KQPWPJQDWZIGMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 4-氯苯甲醛 、 N-甲基苯胺 在 Yb(OTf)3-SiO₂ 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到N-((4-chlorophenyl)(1-methyl-1H-indol-3-yl)methyl)-N-methylbenzenamine
  参考文献：
  名称：

  3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities

  摘要：

  An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf)(3)-SiO2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 mu M. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC50 values of 50.6 and 58.3 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.010

文献信息

• Efficient metal-free green syntheses of 4<i>H</i>-chromenes and 3-amino alkylated indoles using a reusable graphite oxide carbocatalyst under aqueous and solvent-free reaction conditions
  作者：Lenida Kyndiah、Fillip Kumar Sarkar、Ajay Gupta、Amarta Kumar Pal

  DOI：10.1039/d2nj00756h

  日期：——

  Graphite oxide (GO) was utilized for the one-pot three-component syntheses of pharmaceutically important 4H-chromenes and 3-amino alkylated indoles in water and solvent-free reaction conditions, respectively. Spectroscopic techniques such as FT-IR, XPS, SEM, TEM, SAED, EDX, PXRD, Raman, and TGA confirmed the formation and thermal stability of GO. These protocols provide green and sustainable reaction

  氧化石墨 (GO) 分别用于在水和无溶剂反应条件下一锅三组分合成药学上重要的 4 H-色烯和 3-氨基烷基化吲哚。FT-IR、XPS、SEM、TEM、SAED、EDX、PXRD、拉曼和 TGA 等光谱技术证实了 GO 的形成和热稳定性。这些协议提供了绿色和可持续的反应条件，包括优异的催化活性、良好的产品产率、催化剂的可重复使用性、高官能团耐受性和克级合成。此外，本方法排除了金属毒性、金属废物处理、产品中的金属污染以及挥发性有机溶剂的使用等问题。
• 3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities
  作者：V. Kameshwara Rao、Bhupender S. Chhikara、Amir Nasrolahi Shirazi、Rakesh Tiwari、Keykavous Parang、Anil Kumar

  DOI：10.1016/j.bmcl.2011.05.010

  日期：2011.6

  An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf)(3)-SiO2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 mu M. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC50 values of 50.6 and 58.3 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.