[(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-acetonitrile | 98634-61-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-acetonitrile
• CAS: 98634-61-8
• 化学式: C₁₉H₁₇F₂N₃
• 分子量: 325.361
• InChiKey: LFNIOYIAZAYUJI-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  30.27
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-acetonitrile 在 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4a,9b-trans-8-fluoro-5-(4-fluorophenyl)-2-<2-(3-hydroxy-2-phenylpropionamido)ethyl>-1,2,3,4,4a,9b-trans-hexahydro-γ-carboline
  参考文献：
  名称：

  Neuroleptic activity of chiral trans-hexahydro-.gamma.-carbolines

  摘要：

  A series of trans-8-fluoro-5-(4-fluorophenyl)-2,3,4,4a,5, 9b-hexahydro-1H-pyrido[4,3-b]indoles with various N-2 substituents has been prepared and tested for neuroleptic activity [( 3H]spiroperidol binding and amphetamine antagonism). Several members of this series showed exceptional in vivo potency, especially the hydantoin derivatives 27-30. Resolution into the enantiomers showed that neuroleptic activity is associated with the 4aS,9bS absolute configuration. These rigid neuroleptics have been correlated with other rigid neuroleptics [(+)-dexclamol, Ro 22-1319] and can serve to further define the topography of the dopamine receptor.

  DOI：

  10.1021/jm00151a002
• 作为产物：
  描述：

  氯乙腈 、 (-)-4a,9b-trans-8-fluoro-5-(4-fluorophenyl)-1,2,3,4,4a,9b-hexahydro-γ-carboline 在 sodium carbonate 、 potassium iodide 作用下， 以 various solvent(s) 为溶剂， 以71%的产率得到[(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-acetonitrile
  参考文献：
  名称：

  Neuroleptic activity of chiral trans-hexahydro-.gamma.-carbolines

  摘要：

  A series of trans-8-fluoro-5-(4-fluorophenyl)-2,3,4,4a,5, 9b-hexahydro-1H-pyrido[4,3-b]indoles with various N-2 substituents has been prepared and tested for neuroleptic activity [( 3H]spiroperidol binding and amphetamine antagonism). Several members of this series showed exceptional in vivo potency, especially the hydantoin derivatives 27-30. Resolution into the enantiomers showed that neuroleptic activity is associated with the 4aS,9bS absolute configuration. These rigid neuroleptics have been correlated with other rigid neuroleptics [(+)-dexclamol, Ro 22-1319] and can serve to further define the topography of the dopamine receptor.

  DOI：

  10.1021/jm00151a002