(2-amino-6-methoxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(3,4,5-trimethoxyphenyl)methanone | 939970-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-6-methoxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (2-Amino-6-methoxy-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 939970-49-7
• 化学式: C₁₉H₂₃NO₅S
• 分子量: 377.461
• InChiKey: FWFYCRBNHUYNMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-amino-6-methoxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(3,4,5-trimethoxyphenyl)methanone 在 palladium on activated charcoal 吡啶 、 水 作用下， 反应 22.0h， 生成 N-[6-methoxy-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
• 作为产物：
  描述：

  4-甲氧基环己酮 、 3,4,5-三甲氧基苯甲酰乙腈 在 吗啉 、 sulfur 作用下， 反应 21.0h， 以64%的产率得到(2-amino-6-methoxy-4,5,6,7-tetrahydrobenzo[b]thiophen-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