(3-amino-6-methoxy-1H-indol-2-yl)-(3,4,5-trimethoxyphenyl)methanone | 1012370-00-1

• 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: (3-amino-6-methoxy-1H-indol-2-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1012370-00-1
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: QAPKTFCUIZZQKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯酐 、 (3-amino-6-methoxy-1H-indol-2-yl)-(3,4,5-trimethoxyphenyl)methanone 在 溶剂黄146 作用下， 反应 18.0h， 以80%的产率得到2-[6-methoxy-2-(3,4,5-trimethoxybenzoyl)-1H-indol-3-yl]-isoindole-1,3-dione
  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
• 作为产物：
  描述：

  1-ethoxycarbonyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-6-methoxy-1H-indole 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以62%的产率得到(3-amino-6-methoxy-1H-indol-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

• 3‐Aminoindole Synthesis from 2‐Nitrochalcones and Ammonia or Primary Amines
  作者：Guan Zhang、Lu Lin、Kai Yang、Shihui Wang、Qiang Feng、Jun Zhu、Qiuling Song

  DOI：10.1002/adsc.201900551

  日期：2019.8.21

  A step‐economic strategy for 3‐aminoindoles synthesis with ammonia or primary amines as “N” source under transition‐metal‐free conditions was achieved. A series of 3‐aminoindoles was obtained with abundant “N” source featuring high efficiency, mild conditions, environmental friendliness and scalability. Efficient syntheses of the intermediates of COX‐2 inhibitor and tubulin polymerization inhibitor

  在无过渡金属的条件下，实现了以氨或伯胺为“ N”源的3-氨基吲哚合成的分步经济策略。获得了一系列3-氨基吲哚，其中含有丰富的“ N”源，具有高效率，温和的条件，环境友好性和可扩展性。通过这种新开发的策略，成功完成了COX-2抑制剂和微管蛋白聚合抑制剂中间体的高效合成。
• 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.