((S)-1-Methyl-2-phenyl-ethyl)-phenethyl-amine | 132076-48-3

• 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: ((S)-1-Methyl-2-phenyl-ethyl)-phenethyl-amine
• 英文别名: (2S)-1-phenyl-N-(2-phenylethyl)propan-2-amine
• CAS: 132076-48-3
• 化学式: C₁₇H₂₁N
• 分子量: 239.36
• InChiKey: MRVIUBHXZKIUJZ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 ((S)-1-Methyl-2-phenyl-ethyl)-phenethyl-amine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以49%的产率得到(S)-(+)-N-benzyl-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：

  右旋苯丙胺 、 苯乙醛 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 ((S)-1-Methyl-2-phenyl-ethyl)-phenethyl-amine
  参考文献：
  名称：

  Identification and exploitation of the .sigma.-opiate pharmacophore

  摘要：

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.

  DOI：

  10.1021/jm00107a033

文献信息

• New bronchospasmolytic compounds and process for their preparation
  申请人：Aktiebolaget Draco

  公开号：EP0390762B1

  公开（公告）日：1994-01-19
• Identification and exploitation of the .sigma.-opiate pharmacophore
  作者：Richard A. Glennon、J. Doyle Smith、Abd M. Ismaiel、Mahmoud El-Ashmawy、George Battaglia、James B. Fischer

  DOI：10.1021/jm00107a033

  日期：1991.3

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.
• Structural Features Important for .sigma.1 Receptor Binding
  作者：Richard A. Glennon、Seth Y. Ablordeppey、Abd M. Ismaiel、Mahmoud B. El-Ashmawy、James B. Fischer、Kathleen Burke Howie

  DOI：10.1021/jm00034a020

  日期：1994.4

  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.