8-fluoro-5-(4-fluorophenyl)-2-methyl-1,2,3,4-tetrahydro-γ-carboline | 73586-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 8-fluoro-5-(4-fluorophenyl)-2-methyl-1,2,3,4-tetrahydro-γ-carboline
• 英文别名: 8-Fluor-5-(p-fluorphenyl)-2-methyl-1,2,3,4-tetrahydro-γ-carbolin；8-fluoro-5-(4-fluoro-phenyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；8-fluoro-5-(4-fluorophenyl)-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole
• CAS: 73586-19-3
• 化学式: C₁₈H₁₆F₂N₂
• 分子量: 298.335
• InChiKey: UMCAIVDDVZHPAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-氟-1,3,4,5-四氢-2H-吡啶基-[4,3-b]吲哚-2-羧酸乙酯 在 aluminium hydride 、 sodium carbonate 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.5h， 生成 8-fluoro-5-(4-fluorophenyl)-2-methyl-1,2,3,4-tetrahydro-γ-carboline
  参考文献：
  名称：

  Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines

  摘要：

  A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.

  DOI：

  10.1021/jm00180a011

文献信息

• HARBERT C. A.; PLATTNER J. J.; WELCH W. M.; WEISSMAN A.; KOE B. K., J. MED. CHEM., 1980, 23, NO 6, 635-643
  作者：HARBERT C. A.、 PLATTNER J. J.、 WELCH W. M.、 WEISSMAN A.、 KOE B. K.

  DOI：——

  日期：——
• Substituted 2,3,4,5-Tetrahyrdo-1H-Pyrido[4,3-B]Indoles, Methods for the Production and Use Thereof
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US20100120792A1

  公开（公告）日：2010-05-13

  The invention relates to antagonists of serotonin 5-HT 6 receptors simultaneously regulating homeostasis of Ca +2 ions in cells, representing substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles of the general formula 1, pharmaceutically acceptable salts and/or hydrate thereof. In the general formula 1: R 1 represents amino group substituent selected from optionally substituted C 1 -C 5 alkyl; R 2 , is one or more substituents selected from hydrogen, halogen, C 1 -C 3 alkyl, CF 3 , OCF 3 ; Ar is phenyl optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, substituted amino group, or CF 3 ; or optionally substituted aromatic 6-membered heterocycle comprising 1-2 nitrogen atoms in the cycle; W represents ethylene group —CH 2 —CH 2 —, ethenyl group —CH═CH—, or ethynyl group —C≡C—. The invention also relates to the novel compounds selected from the compounds of the general formula 1, methods for their preparation, pharmaceutical compositions and methods of their use.
• Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines
  作者：Charles A. Harbert、Jacob J. Plattner、Willard M. Welch、Albert Weissman、B. Kenneth Koe

  DOI：10.1021/jm00180a011

  日期：1980.6

  A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.