ethyl 5,6-dimethoxy-3-methylbenzo-(b)-furan-2-carboxylate | 86624-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 5,6-dimethoxy-3-methylbenzo-(b)-furan-2-carboxylate
• 英文别名: Ethyl 5,6-dimethoxy-3-methyl-1-benzofuran-2-carboxylate
• CAS: 86624-97-7
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: WTUUWTLMUFCUIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5,6-dimethoxy-3-methylbenzo-(b)-furan-2-carboxylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以88%的产率得到5,6-二甲氧基-3-甲基-1-苯并呋喃-2-羧酸
  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'-羟基-4',5'-二甲氧基苯乙酮 在 sodium methylate 、 potassium carbonate 作用下， 生成 ethyl 5,6-dimethoxy-3-methylbenzo-(b)-furan-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

文献信息

• Heterocycles from 2-Aminopyridine and Derivatives of 3-Methylbenzofuran-2-carboxylic Acid
  作者：Yvette A. Jackson、Mark F. Williams

  DOI：10.3987/com-96-7660

  日期：——
• Box, Vernon G. S.; Jackson, Yvette A., Heterocycles, 1983, vol. 20, # 5, p. 753 - 760
  作者：Box, Vernon G. S.、Jackson, Yvette A.

  DOI：——

  日期：——
• BOX, V. G. S.;JACKSON, Y. A., HETEROCYCLES, 1983, 20, N 5, 753-760
  作者：BOX, V. G. S.、JACKSON, Y. A.

  DOI：——

  日期：——
• 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.