ethyl 5-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate | 145389-11-3

• 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: ethyl 5-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate
• 英文别名: Ethyl 5-hydroxy-3-methyl-1-benzothiophene-2-carboxylate；ethyl 5-hydroxy-3-methyl-1-benzothiophene-2-carboxylate
• CAS: 145389-11-3
• 化学式: C₁₂H₁₂O₃S
• 分子量: 236.291
• InChiKey: CGRCGABPYDQKCI-UHFFFAOYSA-N

物化性质

• 沸点：
  386.3±37.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate 在 溴 、 溶剂黄146 作用下， 反应 16.0h， 以30%的产率得到ethyl 4,6-dibromo-5-hydroxy-3-methylbenzo[b] thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues

  摘要：

  5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free, dynamic mass redistribution and Tango beta-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

  DOI：

  10.1021/ml300076u
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲醛 在 18-冠醚-6 、 三溴化硼 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 ethyl 5-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  [EN] GPR35 LIGANDS AND THE USES THEREOF
  [FR] LIGANDS DE GPR35 ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2013022740A3

文献信息

• [EN] GPR35 LIGANDS AND THE USES THEREOF<br/>[FR] LIGANDS DE GPR35 ET LEURS UTILISATIONS
  申请人：CORNING INC

  公开号：WO2013022740A3

  公开（公告）日：2013-05-10
• Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues
  作者：Huayun Deng、Ye Fang

  DOI：10.1021/ml300076u

  日期：2012.7.12

  5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free, dynamic mass redistribution and Tango beta-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.