3-[2-(4-Methyl-piperazin-1-yl)-ethyl]-1H-indol-4-ol | 59044-64-3

• 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: 3-[2-(4-Methyl-piperazin-1-yl)-ethyl]-1H-indol-4-ol
• 英文别名: 3-[2-(4-methylpiperazin-1-yl)ethyl]-1H-indol-4-ol
• CAS: 59044-64-3
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: OOWKQSMXJCKWOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苄氧基吲哚 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 生成 3-[2-(4-Methyl-piperazin-1-yl)-ethyl]-1H-indol-4-ol
  参考文献：
  名称：

  SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist

  摘要：

  An SAR study of psilocybin and psilocin derivatives reveals that 1-methylpsilocin is a selective agonist at the h5-HT2C receptor. The corresponding phosphate derivative, 1-methylpsilocybin, shows efficacy in an animal model for obsessive-compulsive disorder, as does 4-fluoro-N,N-dimethyltryptamine. These results suggest a new area for development of novel 5-HT2C agonists with applications for drug discovery. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.104

文献信息

• Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(<i>N</i>-methyl-<i>N</i>-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols
  作者：David B. Repke、Wilfred J. Ferguson、Dallas K. Bates

  DOI：10.1002/jhet.5570180131

  日期：1981.1

  Structural alteration of the Nb-substituents of psilocin (3-[2-dimethylamino)ethyl]indol-4-ol) (12a) has led to a number of compounds containing known pharmacophoric groups. Further, it is hoped that the subtle changes in the nature of these substituents may lead to a clearer understanding of the structure-activity relationships of the 4-hydroxytryptamine hallucinogens.

  psilocin（3- [2-二甲基氨基）乙基]吲哚-4-醇（12a）的N b-取代基的结构改变导致许多化合物含有已知的药效基团。此外，希望这些取代基的性质的细微变化可以导致对4-羟基色胺致幻剂的结构-活性关系的更清楚的理解。
• SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist
  作者：Howard Sard、Govindaraj Kumaran、Cynthia Morency、Bryan L. Roth、Beth Ann Toth、Ping He、Louis Shuster

  DOI：10.1016/j.bmcl.2005.06.104

  日期：2005.10

  An SAR study of psilocybin and psilocin derivatives reveals that 1-methylpsilocin is a selective agonist at the h5-HT2C receptor. The corresponding phosphate derivative, 1-methylpsilocybin, shows efficacy in an animal model for obsessive-compulsive disorder, as does 4-fluoro-N,N-dimethyltryptamine. These results suggest a new area for development of novel 5-HT2C agonists with applications for drug discovery. (c) 2005 Elsevier Ltd. All rights reserved.