ethyl 5-methoxy-3-methylbenzo[b] thiophene-2-carboxylate | 1380695-55-5

• 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-methoxy-3-methylbenzo[b] thiophene-2-carboxylate
• 英文别名: ethyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate；ethyl 5-methoxy-3-methylbenzothiophene-2-carboxylate；Ethyl 5-methoxy-3-methyl-1-benzothiophene-2-carboxylate；ethyl 5-methoxy-3-methyl-1-benzothiophene-2-carboxylate
• CAS: 1380695-55-5
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: HRJUTVVGAMKFRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-methoxy-3-methylbenzo[b] thiophene-2-carboxylate 在 硝酸 、 溶剂黄146 作用下， 以74%的产率得到ethyl 5-methoxy-3-methyl-4-nitrobenzothiophene-2-carboxylate
  参考文献：
  名称：

  Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1

  摘要：

  A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.071
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲醛 在 18-冠醚-6 、 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 32.0h， 生成 ethyl 5-methoxy-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

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.
• Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1
  作者：Jeffery J. Newsome、Mary Hassani、Elizabeth Swann、Jane M. Bibby、Howard D. Beall、Christopher J. Moody

  DOI：10.1016/j.bmc.2013.03.071

  日期：2013.6

  A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione. (C) 2013 Elsevier Ltd. All rights reserved.