N-[3-(4-methoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide | 864378-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[3-(4-methoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide
• 英文别名: N-[3-(4-methoxybenzoyl)-1-benzothiophen-2-yl]acetamide
• CAS: 864378-40-5
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: SKAGDSZNLPTSHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[3-(4-methoxybenzoyl)-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-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-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：

  (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-methoxyphenyl)methanone 在 吡啶 、 palladium on activated charcoal 、 水 作用下， 反应 18.0h， 生成 N-[3-(4-methoxybenzoyl)-benzo[b]thiophen-2-yl]acetamide
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of new anti-tubulin agents containing different benzoheterocycles

  摘要：

  A new series of compounds, in which the 2-amino-4-methoxyphenyl ring of phenstatin analogue 5 was replaced with 2- or 3-amino-benzoheterocycles, was synthesized and evaluated for antiproliferative activity and inhibition of colchicine binding. The lack of activity of 3 ',4 '-dimethoxy- and 4 '-methoxy-benzoyl derivatives (8 and 9, respectively) indicates that the 3 ',4 ',5 '-trimethoxybenzoyl moiety is critical for the activity. Two compounds, 7 and 11, displayed potent antiproliferative activity, with IC50 values ranging from 25 to 100 nM against a variety of cancer cell lines. Derivative 11 was more active than CA-4 as an inhibitor of tubulin polymerization. The results demonstrated that the antiproliferative activity was correlated with inhibition of tubulin polymerization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.022