3-[1-(8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-piperidin-4-yl]-2-phenyl-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[1-(8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-piperidin-4-yl]-2-phenyl-1H-indole
• 英文别名: 3-(8-azabicyclo[3.2.1]octan-3-yl)-2-phenyl-1H-indole
• 化学式: C₂₁H₂₂N₂
• 分子量: 302.419
• InChiKey: CSPMIMZHBXUYLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙基溴苯 、 3-[1-(8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-piperidin-4-yl]-2-phenyl-1H-indole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  3-(4-Piperidinyl)- and 3-(8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-1H-indoles as bioavailable h5-HT2A antagonists

  摘要：

  A series of 3-(4-piperidinyl)- and 3-(8-aza-bicyclo[3.2.1] oct-3-yl)-2-phenyl-1H-indoles have been prepared and evaluated as ligands for the h5-HT2A receptor. 3-(8-Phenethyl-8-aza-bicyclol[3.2.1]oct-3-yl)-2-phenyl-1H-indole is a high-affinity (1.2 nM), selective (>800 fold over h5-HT2C and hD(2) receptors) antagonist at the h5-HT2A receptor with oral bioavailability in rats. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00559-x

文献信息

• [EN] AZABICYCLE-SUBSTITUTED PHENYLINDOLE DERIVATIVES AS LIGANDS FOR 5-HT2A RECEPTORS<br/>[FR] DERIVES DE PHENYLINDOLE A SUBSTITUTION AZABICYCLIQUE EN TANT QUE LIGANDS DES RECEPTEURS 5-HT2A
  申请人：MERCK SHARP & DOHME

  公开号：WO2000004017A1

  公开（公告）日：2000-01-27

  Compounds of formula (I), or a salt thereof wherein the broken line represents an optional chemical bond; A and B independently represent hydrogen, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy; C1-6alkyl or C1-6alkoxy; or A and B, when attached to adjacent carbon atoms, together represent methylenedioxy; X and Y independently represent hydrogen, halogen, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy or phenyl; Q represents a group of the formula -CH2CH2- or -CH2CH2CH2-; R1 represents hydrogen, C¿1-6?alkyl, or an optionally substituted aryl(C1-6)alkyl, heteroaryl(C1-6)alkyl or C3-7heterocycloalkyl(C1-6)alkyl group; and R?2¿ represents hydrogen, halogen. C¿1-6?alkyl, hydroxy or C1-6alkoxy are selective antagonists of the human 5-HT2A receptor and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of adverse conditions of the central nervous system, including psychotic disorders such as schizophrenia.
• [EN] NOVEL PROCESSES<br/>[FR] PROCEDES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2001014374A2

  公开（公告）日：2001-03-01

  Novel processes for the stereoselective preparation of exo- and endo- indolotropanes of formulae (IA) and (IB) wherein: R1 is hydrogen or (C¿1-6?)alkyl; R?2 and R3¿, which may be the same or different, are selected from the group consisting of hydrogen, halogen, cyano, (C¿1-6?)alkyl, (C3-7)cycloalkyl, (C1-6)alkoxy, halo(C1-6)alkyl, hydroxy, oxo, amino, mono- or di-(C1-6)alkylamino, acylamino, nitro, carboxy, (C1-6)alkoxycarbonyl, (C1-6)alkenyloxycarbonyl, (C1-6)alkoxycarbonyl(C1-6)alkyl, carboxy(C1-6)alkyl, (C1-6)alkylcarbonyloxy, carboxy(C1-6)alkyloxy, (C1-6)alkoxycarbonyl(C1-6)alkoxy, (C1-6)alkylthio, (C1-6)alkylsulphinyl, (C1-6)alkylsulphonyl, sulphamoyl, mono- and di-(C1-6)-alkylsulphamoyl, carbamoyl, mono- and di-(C1-6)alkylcarbamoyl, (C1-6)alkylsulphonamido, arylsulphonamido, aryl, aryl(C1-6)alkyl, aryl(C1-6)alkoxy, aryloxy, and heterocyclyl; Y is hydrogen, a nitrogen protecting group or an organic substituent; and Nq represents optional ring nitrogen atoms in positions 4, 5, 6, and 7; wherein q is O, 1 or 2.