2-amino-6-(4-hydroxyphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide | 1297474-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-amino-6-(4-hydroxyphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
• CAS: 1297474-37-3
• 化学式: C₁₅H₁₆N₂O₂S
• 分子量: 288.37
• InChiKey: UECYJSQLCHVILP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 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：
  0.27
• 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)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 在 盐酸 、 水 、 四氯苯醌 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 正丁醇 为溶剂， 反应 9.0h， 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：

  4-(4-羟基苯基)环己酮 、 氰乙酰胺 在 哌啶 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-amino-6-(4-hydroxyphenyl)-4,5,6,7-tetrahydrobenzo[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

文献信息

• Tetrahydrobenzothiophene carboxamides: Beyond the kinase domain and into the fatty acid realm
  作者：Sabin Llona-Minguez、Shabnam Fayezi、Alireza Alihemmati、Jordi Juárez-Jiménez、F. Javier Piedrafita、Thomas Helleday

  DOI：10.1016/j.bmcl.2017.08.006

  日期：2017.9

  A series of tetrahydrobenzothiophene carboxamides, inspired by structural features present in kinase and SCD1 inhibitors, are presented here. Prototype compound 8 (MMDD13) modulates fatty acid elongase and desaturase indexes, lipid accumulation, while preserving kinase inhibitory activity. This chemotype represents a stepping stone towards chemical probes to study the consequences of lipid metabolism modulation through non-redundant pathways. (C) 2017 Elsevier Ltd. All rights reserved.