N-[6-methyl-3-(3,4,5-trimethoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide | 939970-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[6-methyl-3-(3,4,5-trimethoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide
• 英文别名: N-[6-methyl-3-(3,4,5-trimethoxybenzoyl)-1-benzothiophen-2-yl]acetamide
• CAS: 939970-54-4
• 化学式: C₂₁H₂₁NO₅S
• 分子量: 399.467
• InChiKey: RREXLSRNVAJJKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[6-methyl-3-(3,4,5-trimethoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以56%的产率得到(2-Amino-6-methyl-1-benzothiophen-3-yl)-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[b]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization

  摘要：

  Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.

  DOI：

  10.1021/jm070050f
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰乙腈 在 palladium on activated charcoal 吗啉 、 吡啶 、 水 、 sulfur 作用下， 反应 43.0h， 生成 N-[6-methyl-3-(3,4,5-trimethoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[b]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization

  摘要：

  Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.

  DOI：

  10.1021/jm070050f