ethyl 6-hexylthieno[3,2-b]thiophene-2-carboxylate | 1313597-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: ethyl 6-hexylthieno[3,2-b]thiophene-2-carboxylate
• CAS: 1313597-93-1
• 化学式: C₁₅H₂₀O₂S₂
• 分子量: 296.455
• InChiKey: LUAKUYFODRPXFM-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  ethyl 6-hexylthieno[3,2-b]thiophene-2-carboxylate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 6-hexylthieno[3,2-b]thiophene-2-carboxylic acid
  参考文献：
  名称：

  Discovery of 2-(4-Methylfuran-2(5H)-ylidene)malononitrile and Thieno[3,2-b]thiophene-2-carboxylic Acid Derivatives as G Protein-Coupled Receptor 35 (GPR35) Agonists

  摘要：

  Screening with dynamic mass redistribution (DMR) assays in a native cell line HT-29 led to identification of two novel series of chemical compounds, 2-(4-methylfuran-2(5H)-ylidene)malononitrile and thieno[3,2-b]thiophene-2-carboxylic. acid derivatives, as GPR35 agonists. Of these, 2-(3-cyano-5-(3,4-dichlorophenyl)-4,5-dimethylfuran-2(5H)-ylidene)malononitrile (YE120) and 6-bromo-3-methylthieno[3,2-b]thiophene-2-carboxylic acid (YE210) were found to be the two most potent GPR35 agonists with an EC50 of 32.5 +/- 1.7 nM and 63.7 +/- 4.1 nM, respectively. Both agonists exhibited better potency than that of zaprinast, a known GPR35 agonist. DMR antagonist assays, knockdown of GPR35 with interference RNA, receptor internalization assays, and Tango beta-arrestin translocation assays confirmed that the agonist activity of these ligands is specific to GPR35. The present study provides novel chemical series as a starting point for further investigations of GPR35 biology and pharmacology.

  DOI：

  10.1021/jm200999f
• 作为产物：
  描述：

  3-bromo-4-hexylthiophene-2-carbaldehyde 、 巯基乙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 6-hexylthieno[3,2-b]thiophene-2-carboxylate
  参考文献：
  名称：

  Discovery of 2-(4-Methylfuran-2(5H)-ylidene)malononitrile and Thieno[3,2-b]thiophene-2-carboxylic Acid Derivatives as G Protein-Coupled Receptor 35 (GPR35) Agonists

  摘要：

  Screening with dynamic mass redistribution (DMR) assays in a native cell line HT-29 led to identification of two novel series of chemical compounds, 2-(4-methylfuran-2(5H)-ylidene)malononitrile and thieno[3,2-b]thiophene-2-carboxylic. acid derivatives, as GPR35 agonists. Of these, 2-(3-cyano-5-(3,4-dichlorophenyl)-4,5-dimethylfuran-2(5H)-ylidene)malononitrile (YE120) and 6-bromo-3-methylthieno[3,2-b]thiophene-2-carboxylic acid (YE210) were found to be the two most potent GPR35 agonists with an EC50 of 32.5 +/- 1.7 nM and 63.7 +/- 4.1 nM, respectively. Both agonists exhibited better potency than that of zaprinast, a known GPR35 agonist. DMR antagonist assays, knockdown of GPR35 with interference RNA, receptor internalization assays, and Tango beta-arrestin translocation assays confirmed that the agonist activity of these ligands is specific to GPR35. The present study provides novel chemical series as a starting point for further investigations of GPR35 biology and pharmacology.

  DOI：

  10.1021/jm200999f