(1R,2R)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (1R,2R)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine
• 英文别名: 1-(2,4-dichlorophenyl)-4-[[(1R,2R)-2-phenylcyclopropyl]methyl]piperazine
• 化学式: C₂₀H₂₂Cl₂N₂
• 分子量: 361.314
• InChiKey: AOSAPZYJOHCROI-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2,4-二氯苯基)哌嗪 在 aluminium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,2R)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine
  参考文献：
  名称：

  trans-1-[(2-Phenylcyclopropyl)methyl]-4-arylpiperazines:  Mixed Dopamine D₂/D₄ Receptor Antagonists as Potential Antipsychotic Agents

  摘要：

  The dopaminergic receptor profile of a series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines was examined. Aromatic substitution patterns were varied with the goal of identifying a compound having affinities for the D-2 and D-4 receptors in a ratio similar to that observed for the atypical neuroleptic clozapine. The compounds (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine (5m) and (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine (5t) were selected for functional antagonists at D-2 and D-4 receptors and had a D-2/D-4 ratio approximating that of clozapine; they proved inactive in behavioral tests of antipsychotic activity.

  DOI：

  10.1021/jm990562x

文献信息

• 1-phenyl-4-(1-[2-aryl]cyclopropyl) methylpiperazines: dopamine receptor ligands
  申请人：Neurogen Corporation

  公开号：US20020022630A1

  公开（公告）日：2002-02-21

  Disclosed are compounds of the formula: 1 or pharmaceutically acceptable addition salts thereof wherein: R 1 , R 2 , R 3 R 4 and R 5 , R 6 , R 7 , and R 8 represent organic and/or inorganic substituents as defined herein, which compounds are useful for the treatment and/or prevention of neuropsychological disorders including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents.

  本发明涉及以下式子的化合物或其药学上可接受的盐：1其中：R1、R2、R3、R4和R5、R6、R7和R8代表有机和/或无机取代基，如本文所定义，这些化合物对于治疗和/或预防神经心理障碍非常有用，包括但不限于精神分裂症、躁狂症、痴呆、抑郁症、焦虑症、强迫行为、物质滥用、帕金森样运动障碍和与神经阻滞剂使用有关的运动障碍。
• US6284761B1
  申请人：——

  公开号：US6284761B1

  公开（公告）日：2001-09-04
• <i>trans</i>-1-[(2-Phenylcyclopropyl)methyl]-4-arylpiperazines:  Mixed Dopamine D₂/D₄ Receptor Antagonists as Potential Antipsychotic Agents
  作者：Xiaoyan Zhang、Kevin Hodgetts、Stanislaw Rachwal、He Zhao、Jan W. F. Wasley、Kimberly Craven、Robbin Brodbeck、Andrzej Kieltyka、Diane Hoffman、Maria D. Bacolod、Brian Girard、Jennifer Tran、Andrew Thurkauf

  DOI：10.1021/jm990562x

  日期：2000.10.1

  The dopaminergic receptor profile of a series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines was examined. Aromatic substitution patterns were varied with the goal of identifying a compound having affinities for the D-2 and D-4 receptors in a ratio similar to that observed for the atypical neuroleptic clozapine. The compounds (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine (5m) and (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine (5t) were selected for functional antagonists at D-2 and D-4 receptors and had a D-2/D-4 ratio approximating that of clozapine; they proved inactive in behavioral tests of antipsychotic activity.