5-benzyloxy-3-dimethylaminoethyl-1-phenylindole | 297751-70-3

• 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: 5-benzyloxy-3-dimethylaminoethyl-1-phenylindole
• 英文别名: N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine；2-[1-(benzenesulfonyl)-5-phenylmethoxyindol-3-yl]-N,N-dimethylethanamine
• CAS: 297751-70-3
• 化学式: C₂₅H₂₆N₂O₃S
• 分子量: 434.559
• InChiKey: PLQFOHQKYPNKGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-dimethylaminoethyl-1-phenylindole 在 catalyst 、 氢氧化钯 Ammonia methanol dichloromethane 、 silica gel 、 乙醚 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以to give the title compound as a crystalline solid after trituration with diethyl ether (30 ml)的产率得到N,N-dimethyl 2-(1-benzenesulphonyl-5-hydroxy-1H-indol-3-yl)ethylamine
  参考文献：
  名称：

  Indole and indoline derivatives as 5-HT6 selective ligands

  摘要：

  公开了三类吲哚和吲哚啉衍生物作为选择性5-HT6受体配体，因此对于治疗或预防中枢神经系统疾病，包括阿尔茨海默病、帕金森病、精神分裂症、抑郁症和焦虑症具有价值。其中一类为1-取代-4-(&ohgr;-N,N-二烷基-氨基烷基)吲哚，被认为是新型化合物。

  公开号：

  US06187805B1
• 作为产物：
  描述：

  N,N-二甲基-5-(苄氧基)-1H-吲哚-3-乙胺 、 苯磺酰氯 在 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 5-benzyloxy-3-dimethylaminoethyl-1-phenylindole
  参考文献：
  名称：

  N-Arylsulfonylindole Derivatives as Serotonin 5-HT₆ Receptor Ligands

  摘要：

  A series of N-1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yI in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.

  DOI：

  10.1021/jm010943m

文献信息

• Use
  申请人：——

  公开号：US20030139424A1

  公开（公告）日：2003-07-24

  The invention provides a method of treatment or prophylaxis of obesity or for the reduction of food intake, comprising administering to a patient in need of such treatment a therapeutically effective amount of an indole or indoline derivative of Formula I, II or III: 1 wherein the substituents are as described in the specification.

  本发明提供了一种治疗或预防肥胖或减少食物摄入的方法，包括向需要此类治疗的患者给予公式I、II或III的吲哚或吲哚啉衍生物的治疗有效量：1其中取代基如说明书所述。
• Indole and indoline derivatives as 5-HT6 selective ligands
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06187805B1

  公开（公告）日：2001-02-13

  Three classes of indole and indoline derivatives are disclosed as ligands selective for the 5-HT6 receptors, and hence of value in the treatment or prevention of CNS disorders, including Alzheimer's disease, Parkinson's disease, schizophrenia, depression and anxiety. A particular class, 1-substituted-4-(&ohgr;-N,N-dialkyl-aminoalkyl)indoles, are claimed as novel compounds.

  公开了三类吲哚和吲哚啉衍生物作为选择性5-HT6受体配体，因此对于治疗或预防中枢神经系统疾病，包括阿尔茨海默病、帕金森病、精神分裂症、抑郁症和焦虑症具有价值。其中一类为1-取代-4-(&ohgr;-N,N-二烷基-氨基烷基)吲哚，被认为是新型化合物。
• Lee; Rangisetty; Dukat, Medicinal Chemistry Research, 2000, vol. 10, # 4, p. 230 - 242
  作者：Lee、Rangisetty、Dukat、Slassi、Maclean、Lee、Glennon

  DOI：——

  日期：——
• USE OF INDOLE AND INDOLINE DERIVATIVES IN THE TREATMENT OF OBESITY OR FOR THE REDUCTION OF FOOD INTAKE
  申请人：BIOVITRUM AB

  公开号：EP1438045A1

  公开（公告）日：2004-07-21
• US6187805B1
  申请人：——

  公开号：US6187805B1

  公开（公告）日：2001-02-13