N-[3-(4-methoxybenzoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl]acetonitrile | 939970-51-1

• 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)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl]acetonitrile
• 英文别名: N-[3-(4-methoxybenzoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]acetamide
• CAS: 939970-51-1
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: OKKNCISNZFVREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl]acetonitrile 在 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
• 作为产物：
  描述：

  4-甲氧基苯甲酰基乙腈 在 吗啉 、 吡啶 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 N-[3-(4-methoxybenzoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl]acetonitrile
  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

文献信息

• Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[<i>b</i>]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Delia Preti、Francesca Fruttarolo、Maria Giovanna Pavani、Mojgan Aghazadeh Tabrizi、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Jan Balzarini、John A. Hadfield、Andrea Brancale、Ernest Hamel

  DOI：10.1021/jm070050f

  日期：2007.5.1

  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.