(R)-(-)-N-(2-phenoxyethyl)-1-phenyl-2-aminopropane hydrochloride | 132017-97-1

• 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: (R)-(-)-N-(2-phenoxyethyl)-1-phenyl-2-aminopropane hydrochloride
• 英文别名: (2R)-N-(2-phenoxyethyl)-1-phenylpropan-2-amine;hydrochloride
• CAS: 132017-97-1
• 化学式: C₁₇H₂₁NO*ClH
• 分子量: 291.821
• InChiKey: GMQLHVYUJSVMQF-XFULWGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  左苯丙胺 、 2-氯苯乙醚 反应 20.0h， 以8%的产率得到(R)-(-)-N-(2-phenoxyethyl)-1-phenyl-2-aminopropane hydrochloride
  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

• SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP0507863A1

  公开（公告）日：1992-10-14
• EP0507863A4
  申请人：——

  公开号：EP0507863A4

  公开（公告）日：1993-07-07
• US6057371A
  申请人：——

  公开号：US6057371A

  公开（公告）日：2000-05-02
• [EN] SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：——

  公开号：WO1991009594A1

  公开（公告）日：1991-07-11

  [EN] The invention relates to methods for the treatment of schizophrenia or other psychoses by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof.
  [FR] Procédés de traitement de la schizophrénie ou d'autres psychoses, par administration d'une composition pharmaceutique comprenant une quantité efficace de certains ligands de récepteur sigma, à un patient nécessitant un tel traitement. L'invention concerne également de nouveaux ligands de récepteur sigma, présentant une liaison élevée aux récepteurs sigma, ainsi que leurs compositions pharmaceutiques.