(2-amino-4-(3,5-bis(trifluoromethyl)phenyl)-5-methylthiophen-3-yl)(phenyl)methanone | 1359871-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-4-(3,5-bis(trifluoromethyl)phenyl)-5-methylthiophen-3-yl)(phenyl)methanone
• 英文别名: [2-Amino-4-[3,5-bis(trifluoromethyl)phenyl]-5-methylthiophen-3-yl]-phenylmethanone
• CAS: 1359871-76-3
• 化学式: C₂₀H₁₃F₆NOS
• 分子量: 429.386
• InChiKey: CKWRHFSLVPKNBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  苯甲酰乙腈 、 3,5-二(三氟甲基)苯丙酮 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 二乙胺 作用下， 反应 1.0h， 以15%的产率得到(2-amino-4-(3,5-bis(trifluoromethyl)phenyl)-5-methylthiophen-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis and Characterization of Novel 2-Amino-3-benzoylthiophene Derivatives as Biased Allosteric Agonists and Modulators of the Adenosine A₁ Receptor

  摘要：

  A series of novel 2-amino-3-benzoylthiophenes (2A3BTs) were screened using a functional assay of AIR mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK1/2) in intact CHO cells to identify potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA. Two derivatives, 8h and 8i, differing only in terms of the absence or presence of an electron-withdrawing group on the benzoyl moiety of the 2A3BT scaffold, were identified as biased allosteric agonists and positive allosteric modulators of agonist function at the adenosine A(1) receptor (A(1)R) in two different functional assays. Our findings indicate that subtle structural variations can promote functionally distinct receptor conformational states.

  DOI：

  10.1021/jm201600e

文献信息

• Synthesis and Characterization of Novel 2-Amino-3-benzoylthiophene Derivatives as Biased Allosteric Agonists and Modulators of the Adenosine A₁ Receptor
  作者：Celine Valant、Luigi Aurelio、Shane M. Devine、Trent D. Ashton、Jonathan M. White、Patrick M. Sexton、Arthur Christopoulos、Peter J. Scammells

  DOI：10.1021/jm201600e

  日期：2012.3.8

  A series of novel 2-amino-3-benzoylthiophenes (2A3BTs) were screened using a functional assay of AIR mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK1/2) in intact CHO cells to identify potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA. Two derivatives, 8h and 8i, differing only in terms of the absence or presence of an electron-withdrawing group on the benzoyl moiety of the 2A3BT scaffold, were identified as biased allosteric agonists and positive allosteric modulators of agonist function at the adenosine A(1) receptor (A(1)R) in two different functional assays. Our findings indicate that subtle structural variations can promote functionally distinct receptor conformational states.