(3-Amino-1,4-dimethylindol-2-yl)-(3,4,5-trimethoxyphenyl)methanone | 1012370-31-8

• 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: (3-Amino-1,4-dimethylindol-2-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1012370-31-8
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: UEIYDYDIZORSCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[1,4-dimethyl-2-(3,4,5-trimethoxybenzoyl)-indol-3-yl]-isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到(3-Amino-1,4-dimethylindol-2-yl)-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Methyl-2-(3′,4′,5′-trimethoxybenzoyl)-3-aminoindoles as a New Class of Antimitotic Agents and Tubulin Inhibitors

  摘要：

  The 2-(3,4,5-trimethoxybenzoyl)-2-aminoindole nucleus was used as the fundamental structure for the synthesis of compounds modified with respect to positions C-4 to C-7 with different moieties (chloro, methyl, or methoxy). Additional structural variations concerned the indole nitrogen, which was alkylated with small alkyl groups such as methyl or ethyl. We have identified 1-methyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-7-methoxyindole as a new highly potent anti proliferative agent that targets tubulin at the colchicine binding site and leads to apoptotic cell death.

  DOI：

  10.1021/jm7011547

文献信息

• Synthesis and Biological Evaluation of 1-Methyl-2-(3′,4′,5′-trimethoxybenzoyl)-3-aminoindoles as a New Class of Antimitotic Agents and Tubulin Inhibitors
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Taradas Sarkar、Maria Dora Carrion、Carlota Lopez Cara、Olga Cruz-Lopez、Delia Preti、Mojgan Aghazadeh Tabrizi、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Nicola Zonta、Jan Balzarini、Andrea Brancale、Hsing-Pang Hsieh、Ernest Hamel

  DOI：10.1021/jm7011547

  日期：2008.3.13

  The 2-(3,4,5-trimethoxybenzoyl)-2-aminoindole nucleus was used as the fundamental structure for the synthesis of compounds modified with respect to positions C-4 to C-7 with different moieties (chloro, methyl, or methoxy). Additional structural variations concerned the indole nitrogen, which was alkylated with small alkyl groups such as methyl or ethyl. We have identified 1-methyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-7-methoxyindole as a new highly potent anti proliferative agent that targets tubulin at the colchicine binding site and leads to apoptotic cell death.