2-amino-6-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide | 1297474-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-amino-6-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide
• CAS: 1297474-46-4
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: HYVSBTMSDHNEGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.34
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-amino-6-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 4.0h， 生成 2-[4-[7-(4-hydroxyphenyl)-4-oxo-3H-[1]benzothiolo[2,3-d]pyrimidin-2-yl]-2-methoxyphenoxy]acetic acid
  参考文献：
  名称：

  Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors

  摘要：

  Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC(50) of 6 mu M for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.081
• 作为产物：
  描述：

  2-amino-6-(4-hydroxyphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 在 四氯苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 2-amino-6-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors

  摘要：

  Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC(50) of 6 mu M for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.081