6-bromo-3-octylthieno[3,2-b]thiophene-2-carboxylic acid | 1313597-96-4

• 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: 6-bromo-3-octylthieno[3,2-b]thiophene-2-carboxylic acid
• 英文别名: 3-n-octyl-6-bromo-thieno[3,2-b]thiophene-2-carboxylic acid；3-Bromo-6-octylthieno[3,2-b]thiophene-5-carboxylic acid
• CAS: 1313597-96-4
• 化学式: C₁₅H₁₉BrO₂S₂
• 分子量: 375.351
• InChiKey: ROIRRXSSPDWUDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  壬酰氯 在 aluminum (III) chloride 、 18-冠醚-6 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-bromo-3-octylthieno[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

文献信息

• COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX
  申请人：Deng Huayun

  公开号：US20120022116A1

  公开（公告）日：2012-01-26

  Disclosed are compositions and methods for the prevention and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for preventing and/or treating diseases which are pathophysiologically related to GPR35 in a subject. The compounds having a formula (I), (II) or (III):

  揭示了与GPR35及/或GPR35-hERG信号复合物在病理生理上相关的疾病的预防和/或治疗的组合物和方法。例如，揭示了用于预防和/或治疗与GPR35在受试者中病理生理相关的疾病的化合物。这些化合物具有以下公式(I)、(II)或(III)：
• [EN] EGFR/VEGFR DUAL MODULATORS AND METHODS OF USING<br/>[FR] MODULATEURS DOUBLES DE EGFR/VEGFR ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CORNING INC

  公开号：WO2011081971A2

  公开（公告）日：2011-07-07

  Disclosed are compositions and methods related to identification of modulators of EGFR and VEGFR.
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT DE TROUBLES PATHOLOGIQUES ASSOCIÉS À GPR35 ET/OU AU COMPLEXE GPR35-HERG
  申请人：CORNING INC

  公开号：WO2012012278A2

  公开（公告）日：2012-01-26

  Disclosed are compositions and methods for the prevention and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for preventing and/or treating diseases which are pathophysiologically related to GPR35 in a subject.
• 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.