6-[[1-(2,2,2-trifluoroethyl)piperidin-4-yl]methoxy]phenanthridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-[[1-(2,2,2-trifluoroethyl)piperidin-4-yl]methoxy]phenanthridine
• 英文别名: 6-[[1-(2,2,2-Trifluoroethyl)piperidin-4-yl]methoxy]phenanthridine
• 化学式: C₂₁H₂₁F₃N₂O
• 分子量: 374.406
• InChiKey: AHJJQSFPLXXEPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-哌啶甲酸甲酯 在 三氟化硼四氢呋喃络合物 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-[[1-(2,2,2-trifluoroethyl)piperidin-4-yl]methoxy]phenanthridine
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061

文献信息

• Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities
  作者：Clement Q. Fontenelle、Zhong Wang、Christine Fossey、Thomas Cailly、Bruno Linclau、Frederic Fabis

  DOI：10.1016/j.bmc.2013.08.061

  日期：2013.12

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.