2-(4-Benzylpiperidin-1-yl)propan-1-ol | 136089-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(4-Benzylpiperidin-1-yl)propan-1-ol
• CAS: 136089-89-9
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: GIVOWRNJEIBODH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苄基哌啶 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 2-(4-Benzylpiperidin-1-yl)propan-1-ol
  参考文献：
  名称：

  Separation of .alpha.1-adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds

  摘要：

  Ifenprodil (1) represents a new class of N-methyl-D-aspartate (NMDA) antagonist. This drug also possesses potent activity at several other brain receptors (most notably alpha-1 adrenergic receptors). We have prepared the enantiomers and diastereomers of ifenprodil along with a series of partial structures in order to explore the basic structure activity relations within this class of compounds. From this study, it is clear that alpha-1 adrenergic and NMDA receptor activities may be separated by selection of the threo relative stereochemistry. Examination of the optical isomers of threo-ifenprodil (2) reveals that no further improvement in receptor selectivity is gained from either antipode. Individual removal of most of the structural fragments from the ifenprodil molecule generally results in less active compounds although fluorinated derivative 9 with threo relative stereochemistry is somewhat more potent and substantially more selective for the NMDA receptor. Finally a minimum structure for activity in this series (14) has been identified. This stripped-down version of ifenprodil possesses nearly equivalent affinity for the NMDA receptor with no selectivity over alpha-1 adrenergic receptors.

  DOI：

  10.1021/jm00114a018

文献信息

• Separation of .alpha.1-adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds
  作者：B. L. Chenard、I. A. Shalaby、B. K. Koe、R. T. Ronau、T. W. Butler、M. A. Prochniak、A. W. Schmidt、C. B. Fox

  DOI：10.1021/jm00114a018

  日期：1991.10

  Ifenprodil (1) represents a new class of N-methyl-D-aspartate (NMDA) antagonist. This drug also possesses potent activity at several other brain receptors (most notably alpha-1 adrenergic receptors). We have prepared the enantiomers and diastereomers of ifenprodil along with a series of partial structures in order to explore the basic structure activity relations within this class of compounds. From this study, it is clear that alpha-1 adrenergic and NMDA receptor activities may be separated by selection of the threo relative stereochemistry. Examination of the optical isomers of threo-ifenprodil (2) reveals that no further improvement in receptor selectivity is gained from either antipode. Individual removal of most of the structural fragments from the ifenprodil molecule generally results in less active compounds although fluorinated derivative 9 with threo relative stereochemistry is somewhat more potent and substantially more selective for the NMDA receptor. Finally a minimum structure for activity in this series (14) has been identified. This stripped-down version of ifenprodil possesses nearly equivalent affinity for the NMDA receptor with no selectivity over alpha-1 adrenergic receptors.