Ethyl 3-bromo-6-pentadecylthieno[3,2-b]thiophene-5-carboxylate | 924657-19-2

• 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 3-bromo-6-pentadecylthieno[3,2-b]thiophene-5-carboxylate
• CAS: 924657-19-2
• 化学式: C₂₄H₃₇BrO₂S₂
• 分子量: 501.593
• InChiKey: FEISXDIVHDATNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 3-bromo-6-pentadecylthieno[3,2-b]thiophene-5-carboxylate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以59%的产率得到6-bromo-3-pentadecylthieno[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：

  棕榈酰氯 在 aluminum (III) chloride 、 18-冠醚-6 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 3-bromo-6-pentadecylthieno[3,2-b]thiophene-5-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

文献信息

• Polymer having thieno[3,2-b] thiophene moieties statement regarding federally sponsored research or development
  申请人：Li Yuning

  公开号：US20070112171A1

  公开（公告）日：2007-05-17

  A polymer comprising one or more types of repeat units, wherein the polymer includes a substituted thieno[3,2-b]thiophene component A and a different component B in the same type of repeat unit or in different types of repeat units, and wherein the polymer excludes a substituted or unsubstituted thieno[2,3-b]thiophene moiety. The polymer can be used as a semiconductor in electronics such as in organic thin film transistors.
• POLYMER HAVING THIENO[3,2-b] THIOPHENE MOIETIES
  申请人：Li Yuning

  公开号：US20090124788A1

  公开（公告）日：2009-05-14

  A polymer comprising one or more types of repeat units, wherein the polymer includes a substituted thieno[3,2-b]thiophene component A and a different component B in the same type of repeat unit or in different types of repeat units, and wherein the polymer excludes a substituted or unsubstituted thieno[2,3-b]thiophene moiety. The polymer can be used as a semiconductor in electronics such as in organic thin film transistors.
• US7919573B2
  申请人：——

  公开号：US7919573B2

  公开（公告）日：2011-04-05
• US7919574B2
  申请人：——

  公开号：US7919574B2

  公开（公告）日：2011-04-05
• Discovery of 2-(4-Methylfuran-2(5<i>H</i>)-ylidene)malononitrile and Thieno[3,2-<i>b</i>]thiophene-2-carboxylic Acid Derivatives as G Protein-Coupled Receptor 35 (GPR35) Agonists
  作者：Huayun Deng、Haibei Hu、Mingqian He、Jieyu Hu、Weijun Niu、Ann M. Ferrie、Ye Fang

  DOI：10.1021/jm200999f

  日期：2011.10.27

  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.