4-[(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-butyric acid; hydrochloride | 98634-67-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-butyric acid; hydrochloride
• CAS: 98634-67-4
• 化学式: C₂₁H₂₂F₂N₂O₂*ClH
• 分子量: 408.876
• InChiKey: FQTGVRGWJICARG-VKLKMBQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.78
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-环己基苯胺 、 4-[(4aR,9bR)-8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-butyric acid; hydrochloride 在 2-bromo-1-methyl-pyridinium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 114.0h， 以12%的产率得到4a,9b-trans-8-fluoro-5-(4-fluorophenyl)-2-<3-(N-cyclohexyl-N-phenylcarbamoyl)propyl>-1,2,3,4,4a,9b-hexahydro-γ-carboline hydrochloride
  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