Phenylpropionyl-L-pervitin | 14482-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phenylpropionyl-L-pervitin
• 英文别名: N-methyl-3-phenyl-N-[(2S)-1-phenylpropan-2-yl]propanamide
• CAS: 14482-57-6
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: DSWOVGWHVVQFPC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Phenylpropionyl-L-pervitin 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (S)-N-methyl-N-(1-methyl-2-phenylethyl)-3-phenyl-1-aminopropane
  参考文献：
  名称：

  Structural Features Important for .sigma.1 Receptor Binding

  摘要：

  Two problems that have hampered a receptor research are (i) a lack of high-affinity agents and iii) the recent identification Of multiple populations of a receptors (i.e., sigma(1) and sigma(2) sites). Recently, several high-affinity sigma ligands have been identified, and the term superpotent sigma ligands has been coined to describe agents with K-i values of <1 nM. We have previously shown that appropriately N-substituted phenylalkylamines bind at a receptors with high affinity. In the present investigation, we examine the structure-affinity relationships of these phenylalkylamine derivatives for sigma binding and describe some of the first superpotent sigma(1) ligands. A binding model was developed to account for the structural features of the phenylalkylamines that appear to be important for the interaction of these agents with sigma(1) sites.

  DOI：

  10.1021/jm00034a020
• 作为产物：
  描述：

  盐酸脱氧麻黄碱 、 3-苯丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到Phenylpropionyl-L-pervitin
  参考文献：
  名称：

  Structural Features Important for .sigma.1 Receptor Binding

  摘要：

  Two problems that have hampered a receptor research are (i) a lack of high-affinity agents and iii) the recent identification Of multiple populations of a receptors (i.e., sigma(1) and sigma(2) sites). Recently, several high-affinity sigma ligands have been identified, and the term superpotent sigma ligands has been coined to describe agents with K-i values of <1 nM. We have previously shown that appropriately N-substituted phenylalkylamines bind at a receptors with high affinity. In the present investigation, we examine the structure-affinity relationships of these phenylalkylamine derivatives for sigma binding and describe some of the first superpotent sigma(1) ligands. A binding model was developed to account for the structural features of the phenylalkylamines that appear to be important for the interaction of these agents with sigma(1) sites.

  DOI：

  10.1021/jm00034a020

文献信息

• Zusammenhänge zwischen Konfiguration und Verteilungsverhalten bei Aminoacylephedrinen Mitt. zur Auftrennung organischer Basen durch Craig-Verteilung
  作者：H. Schönenberger、R. Brinkmann

  DOI：10.1002/ardp.19662991110

  日期：——

  Diastereomere Aminoacylephedrine lassen sich durch Craig‐Verteilung auftrennen. Das unterschiedliche Verteilungsverhalten dieser Verbindungen beruht auf einer Wechselbeziehung zwischen der Carbonamid‐ und der Hydroxylgruppe, die durch die Konfiguration an den 3 Asymmetriezentren in unterschiedlichem Maße beeinflußt wird.

  非对映氨基酰麻黄碱可以通过克雷格分布进行分离。这些化合物的不同分布行为是基于碳酰胺和羟基之间的相互关系，这在不同程度上受到 3 个不对称中心的构型的影响。