2-cyclohexyl-1-phenyl-2-(pyrrolidin-1-yl)ethanone | 1803168-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyclohexyl-1-phenyl-2-(pyrrolidin-1-yl)ethanone
• 英文别名: alpha-Pcyp；2-cyclohexyl-1-phenyl-2-pyrrolidin-1-ylethanone
• CAS: 1803168-11-7
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: FKEHRWJWTWDTDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  环己基甲基苯基酮 在 aluminum (III) chloride 、 溴 作用下， 以 乙醚 、 苯 为溶剂， 反应 70.0h， 生成 2-cyclohexyl-1-phenyl-2-(pyrrolidin-1-yl)ethanone
  参考文献：
  名称：

  Structural Modification of the Designer Stimulant α-Pyrrolidinovalerophenone (α-PVP) Influences Potency at Dopamine Transporters

  摘要：

  alpha-Pyrrolidinovalerophenone (alpha-PVP, 7) is an illegal synthetic stimulant that is being sold on the clandestine market as "flakka" and "gravel". The potent pharmacological effects of alpha-PVP are presumably mediated by inhibition of dopamine uptake at the dopamine transporter (DAT). However, little is known about how structural modification of alpha-PVP influences activity at DAT. Eleven analogs of alpha-PVP were synthesized and examined for their ability to inhibit uptake of [H-3]clopamine and [H-3]serotonin in rat brain synaptosomes. None of the analogs significantly inhibited [H-3]serotonin uptake when tested at 10 mu M at the serotonin transporter (SERT). All of the analogs behaved as DAT reuptake inhibitors, but potencies varied over a >1500-fold range. Potency was primarily associated with the nature of the alpha-substituent, with the more bulky substituents imparting the highest potency. Expansion of the pyrrolidine ring to a piperidine reduced potency up to 10-fold, whereas conformational constraint in the form of an aminotetralone resulted in the least potent compound. Our study provides the first systematic and comparative structure activity investigation on the ability of alpha-PVP analogs to act as inhibitors of DAT.

  DOI：

  10.1021/acschemneuro.5b00160