(2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique | 25379-26-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique
• 英文别名: (2S,2'R)-acide 2-[(naphth-1-yl)methyl]-3-(tetrahydrofur-2-yl)propanoique；(2S)-2-(naphthalen-1-ylmethyl)-3-[(2R)-oxolan-2-yl]propanoic acid
• CAS: 25379-26-4；115025-92-8；115025-93-9；139240-20-3；139240-21-4；139240-23-6；139240-22-5
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: VEJYFDMNWGFBCT-JKSUJKDBSA-N

物化性质

• 沸点：
  464.2±20.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶、加热、超声处理）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  (2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 在 potassium carbonate 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 0.5h， 生成 2-(diethylamino)ethyl (2S)-2-(naphthalen-1-ylmethyl)-3-[(2R)-oxolan-2-yl]propanoate;oxalic 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
• 作为产物：
  描述：

  (aS,2R)-四氢-a-(1-萘甲基)-2-呋喃丙酸 2-(二乙基氨基)乙酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以76%的产率得到(2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique
  参考文献：
  名称：

  萘呋喃基异构体的最佳异构体（= 2-[（萘-1-基）甲基] -3-（四氢呋喃-2-基）丙酸酯和2-（二乙基氨基）乙酸酯）

  摘要：

  萘呋喃基糠酸酯的光学异构体（= 2-[（Diethylamino）ethyl 2-[（（萘-1-基）甲基]]-3-（四氢呋喃-2-基）丙酸酯）

  DOI：

  10.1002/hlca.19910740818

文献信息

• Isomerès optiques du naftidrofuryl ( = 2-[(naphth-1-yl)méthyl]-3-(tétrahydrofur-2-yl)propanoate de 2-(diéthylamino) éthyle)
  作者：Denis Descours、Didier Festal、Jean-Michel Leger、Alain Carpy

  DOI：10.1002/hlca.19910740818

  日期：1991.12.11

  Optical Isomers of Naftidrofuryl( = 2-(Diethylamino)ethyl 2-[(Naphth-1-yl)methyl]-3-(tetrahydrofur-2-yl)propanoate)

  萘呋喃基糠酸酯的光学异构体（= 2-[（Diethylamino）ethyl 2-[（（萘-1-基）甲基]]-3-（四氢呋喃-2-基）丙酸酯）
• Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor
  作者：Jia Hao、Bo Chen、Yiwu Yao、Murad Hossain、Takafumi Nagatomo、Hequan Yao、Lingyi Kong、Hongbin Sun

  DOI：10.1016/j.bmcl.2012.03.093

  日期：2012.5

  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.