5-(4-methylpiperazin-1-yl)-1-(1-(3,4,5-trimethoxyphenyl)vinyl)-1H-indole | 1620817-20-0

• 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: 5-(4-methylpiperazin-1-yl)-1-(1-(3,4,5-trimethoxyphenyl)vinyl)-1H-indole
• 英文别名: 5-(4-Methylpiperazin-1-yl)-1-[1-(3,4,5-trimethoxyphenyl)ethenyl]indole；5-(4-methylpiperazin-1-yl)-1-[1-(3,4,5-trimethoxyphenyl)ethenyl]indole
• CAS: 1620817-20-0
• 化学式: C₂₄H₂₉N₃O₃
• 分子量: 407.513
• InChiKey: FMBKAYTXCSXBCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methyl-N'-(1-(3,4,5-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 碘苯 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 5.0h， 生成 5-(4-methylpiperazin-1-yl)-1-(1-(3,4,5-trimethoxyphenyl)vinyl)-1H-indole
  参考文献：
  名称：

  Tandem One-Pot Palladium-Catalyzed Coupling of Hydrazones, Haloindoles, and Amines: Synthesis of Amino-N-vinylindoles and Their Effect on Human Colon Carcinoma Cells

  摘要：

  The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp(2)-N bonds were formed through two mechanistically distinct reactions using a single Pd(II)/Pd(0) catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.

  DOI：

  10.1021/jo501315q

文献信息

• Tandem One-Pot Palladium-Catalyzed Coupling of Hydrazones, Haloindoles, and Amines: Synthesis of Amino-<i>N</i>-vinylindoles and Their Effect on Human Colon Carcinoma Cells
  作者：Maxime Roche、Jérôme Bignon、Jean-Daniel Brion、Abdallah Hamze、Mouad Alami

  DOI：10.1021/jo501315q

  日期：2014.8.15

  The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp(2)-N bonds were formed through two mechanistically distinct reactions using a single Pd(II)/Pd(0) catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.