(1S,2S)-(+)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine | 135211-17-5

• 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: (1S,2S)-(+)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine
• 英文别名: (2S)-N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(pyrrolidin-1-yl)cyclohexan-1-amine；(1S,2S)-N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-pyrrolidin-1-ylcyclohexan-1-amine
• CAS: 135211-17-5
• 化学式: C₁₉H₂₈Cl₂N₂
• 分子量: 355.351
• InChiKey: SRRUPDPTTGLICG-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  2-(3,4-二氯苯基)-N-甲基-N-[(1S,2S)-2-(1-吡咯烷基)环己基]乙酰胺盐酸盐(1:1) 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (1S,2S)-(+)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine
  参考文献：
  名称：

  Synthesis and receptor binding of enantiomeric N-substituted cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamines as high-affinity .sigma. receptor ligands

  摘要：

  N-Alkyl-substituted derivatives of (+)- and (-)-cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamine have been synthesized in nine steps in a stereospecific manner starting from cyclohexene oxide. The key step in the reaction sequence involved catalytic hydrogenation of oxime 8 in the presence of PtO2 and AcOH to give the cis diamine (+/-)-7. Most of the compounds in this series exhibited very high affinity at sigma-receptors when tested against [H-3]-(+)-3-PPP, and in general it was observed that the 1R,2S enantiomers bound more potently to sigma-receptors than their corresponding 1S,2R enantiomers. The most potent sigma-ligand found in this class was the unsubstituted derivative (1R,2S)-(-)-4, which exhibited an affinity constant of 0.49 nM. This compound was also found to be very selective for sigma-receptors. It exhibited little or no affinity for kappa-opioid, PCP, and dopamine-D2 receptors. It was also demonstrated that the cis configuration as opposed to the trans configuration of (+)- and (-)-5 was necessary for a higher sigma-receptor affinity.

  DOI：

  10.1021/jm00114a015

文献信息

• Synthesis and receptor binding of enantiomeric N-substituted cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamines as high-affinity .sigma. receptor ligands
  作者：Lilian Radesca、Wayne D. Bowen、Lisa Di Paolo、Brian R. De Costa

  DOI：10.1021/jm00114a015

  日期：1991.10

  N-Alkyl-substituted derivatives of (+)- and (-)-cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamine have been synthesized in nine steps in a stereospecific manner starting from cyclohexene oxide. The key step in the reaction sequence involved catalytic hydrogenation of oxime 8 in the presence of PtO2 and AcOH to give the cis diamine (+/-)-7. Most of the compounds in this series exhibited very high affinity at sigma-receptors when tested against [H-3]-(+)-3-PPP, and in general it was observed that the 1R,2S enantiomers bound more potently to sigma-receptors than their corresponding 1S,2R enantiomers. The most potent sigma-ligand found in this class was the unsubstituted derivative (1R,2S)-(-)-4, which exhibited an affinity constant of 0.49 nM. This compound was also found to be very selective for sigma-receptors. It exhibited little or no affinity for kappa-opioid, PCP, and dopamine-D2 receptors. It was also demonstrated that the cis configuration as opposed to the trans configuration of (+)- and (-)-5 was necessary for a higher sigma-receptor affinity.