10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1H-chromeno[3,4-f]quinolin-5-ol | 1026890-20-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1H-chromeno[3,4-f]quinolin-5-ol
• CAS: 1026890-20-9
• 化学式: C₂₇H₂₄F₃NO₃
• 分子量: 467.488
• InChiKey: AWGLXCLRFBCWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1H-chromeno[3,4-f]quinolin-5-ol 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 16.0h， 生成 2,5-dihydro-10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1H-[1]benzopyrano[3,4-f]quinoline
  参考文献：
  名称：

  Synthesis and Characterization of Non-Steroidal Ligands for the Glucocorticoid Receptor:  Selective Quinoline Derivatives with Prednisolone-Equivalent Functional Activity

  摘要：

  A novel class of functional ligands for the human glucocorticoid receptor is described. Substituents in the C-10 position of the tetracyclic core are essential for glucocorticoid receptor (GR) selectivity versus other steroid receptors. The C-5 position is derivatized with meta-substituted aromatic groups, resulting in analogues with a high affinity for GR (K-i = 2.4-9.3 nM) and functional activity comparable to prednisolone in reporter gene assays of glucocorticoid-mediated gene transcription. The biological activity of these novel quinolines was also prednisolone-equivalent in whole cell assays of glucocorticoid function, and compound 13 was similar to prednisolone (po ED50 = 2.8 mpk for 13 vs ED50 = 1.2 mpk for prednisolone) in a rodent model of asthma (sephadex-induced eosinophil influx).

  DOI：

  10.1021/jm010228c
• 作为产物：
  描述：

  2-溴-5-硝基苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 氢气 、 碘 、 三溴化硼 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 138.0h， 生成 10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1H-chromeno[3,4-f]quinolin-5-ol
  参考文献：
  名称：

  Synthesis and Characterization of Non-Steroidal Ligands for the Glucocorticoid Receptor:  Selective Quinoline Derivatives with Prednisolone-Equivalent Functional Activity

  摘要：

  A novel class of functional ligands for the human glucocorticoid receptor is described. Substituents in the C-10 position of the tetracyclic core are essential for glucocorticoid receptor (GR) selectivity versus other steroid receptors. The C-5 position is derivatized with meta-substituted aromatic groups, resulting in analogues with a high affinity for GR (K-i = 2.4-9.3 nM) and functional activity comparable to prednisolone in reporter gene assays of glucocorticoid-mediated gene transcription. The biological activity of these novel quinolines was also prednisolone-equivalent in whole cell assays of glucocorticoid function, and compound 13 was similar to prednisolone (po ED50 = 2.8 mpk for 13 vs ED50 = 1.2 mpk for prednisolone) in a rodent model of asthma (sephadex-induced eosinophil influx).

  DOI：

  10.1021/jm010228c

文献信息

• Synthesis and Characterization of Non-Steroidal Ligands for the Glucocorticoid Receptor:  Selective Quinoline Derivatives with Prednisolone-Equivalent Functional Activity
  作者：Michael J. Coghlan、Philip R. Kym、Steven W. Elmore、Alan X. Wang、Jay R. Luly、Denise Wilcox、Michael Stashko、Chun-Wei Lin、Jeffrey Miner、Curtis Tyree、Masaki Nakane、Peer Jacobson、Benjamin C. Lane

  DOI：10.1021/jm010228c

  日期：2001.8.1

  A novel class of functional ligands for the human glucocorticoid receptor is described. Substituents in the C-10 position of the tetracyclic core are essential for glucocorticoid receptor (GR) selectivity versus other steroid receptors. The C-5 position is derivatized with meta-substituted aromatic groups, resulting in analogues with a high affinity for GR (K-i = 2.4-9.3 nM) and functional activity comparable to prednisolone in reporter gene assays of glucocorticoid-mediated gene transcription. The biological activity of these novel quinolines was also prednisolone-equivalent in whole cell assays of glucocorticoid function, and compound 13 was similar to prednisolone (po ED50 = 2.8 mpk for 13 vs ED50 = 1.2 mpk for prednisolone) in a rodent model of asthma (sephadex-induced eosinophil influx).