4-[8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-butyric acid ethyl ester | 98634-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-butyric acid ethyl ester
• CAS: 98634-65-2
• 化学式: C₂₃H₂₄F₂N₂O₂
• 分子量: 398.453
• InChiKey: DJUWQCURWXBRNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.47
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-butyric acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 8-fluoro-5-(4-fluorophenyl)-1,2,3,4-tetrahydro-γ-carboline-2-butyric acid
  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：

  4-氯丁酸乙酯 、 8-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 sodium carbonate 、 potassium iodide 作用下， 以 various solvent(s) 为溶剂， 以78%的产率得到4-[8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-butyric acid ethyl ester
  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