(3-amino-6-methyl-1H-indol-2-yl)-(3,4,5-trimethoxyphenyl)methanone | 1012369-96-8

• 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-6-methyl-1H-indol-2-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1012369-96-8
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: UGTAEPITBWMZEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯酐 、 (3-amino-6-methyl-1H-indol-2-yl)-(3,4,5-trimethoxyphenyl)methanone 在 溶剂黄146 作用下， 反应 18.0h， 以78%的产率得到2-[6-methyl-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-methyl-1H-indole 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以61%的产率得到(3-amino-6-methyl-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

• Facile one-pot synthesis, antiproliferative evaluation and structure-activity relationships of 3-amino-1H-indoles and 3-amino-1H-7-azaindoles
  作者：Peng-Cheng Diao、Meng-Jin Hu、Hai-Kui Yang、Wen-Wei You、Pei-Liang Zhao

  DOI：10.1016/j.bioorg.2019.04.008

  日期：2019.7

  A highly efficient method has been developed for the one-pot synthesis of substituted 3-amino-1H-indole and 3-amino-1H-7-azaindole derivatives starting from ethyl 2-cyanophenylcarbamate/ethyl 3-cyanopyridin-2-ylcarbamate, and α-bromoketones in good to excellent yields. All newly synthesized analogues were screened for their antiproliferative activities against four cancer cell lines. The most promising

  从2-氰基苯基氨基甲酸乙酯/ 3-氰基吡啶-2-乙基氨基甲酸乙酯开始，已经开发了一种高效方法，用于一锅合成取代的3-氨基-1H-吲哚和3-氨基-1H-7-氮杂吲哚衍生物。 α-溴酮的收率为好至极好。筛选所有新合成的类似物对四种癌细胞系的抗增殖活性。与氟尿嘧啶相比，最有希望的化合物8v在抑制HeLa，HepG2和MCF-7细胞增殖方面表现出13倍，5倍和1.4倍的改善，IC50值分别为3.7、8.0和19.9μM。此外，8v通过浓度依赖性的方式在HeLa细胞系的G2 / M期诱导了明显的细胞周期停滞。