2-[(naphthalen-1-yl)methyl]-3-[(S)-tetrahydrofuran-2-yl]propanoic acid | 1392400-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[(naphthalen-1-yl)methyl]-3-[(S)-tetrahydrofuran-2-yl]propanoic acid
• CAS: 1392400-74-6
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: VEJYFDMNWGFBCT-LYKKTTPLSA-N

物化性质

• 沸点：
  464.2±20.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-[(naphthalen-1-yl)methyl]-3-[(S)-tetrahydrofuran-2-yl]propanoic acid 在 (S)-(-)- α-甲基苄胺 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 1.0h， 以35%的产率得到(2S,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique
  参考文献：
  名称：

  Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor

  摘要：

  Naftidrofuryl oxalate (Praxilene (R), 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (2-HT2) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT2A receptor, and the C-2' configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT2A receptor that have clinical significance as vasodilators and CNS agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.093
• 作为产物：
  描述：

  (氯甲基)萘 在 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-[(naphthalen-1-yl)methyl]-3-[(S)-tetrahydrofuran-2-yl]propanoic acid
  参考文献：
  名称：

  Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor

  摘要：

  Naftidrofuryl oxalate (Praxilene (R), 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (2-HT2) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT2A receptor, and the C-2' configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT2A receptor that have clinical significance as vasodilators and CNS agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.093