1,3-二乙基-2-甲基-5-硝基-1H-吲哚 | 104621-10-5

• 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
• 中文名称: 1,3-二乙基-2-甲基-5-硝基-1H-吲哚
• 英文名称: 1,3-Diethyl-2-methyl-5-nitroindole
• CAS: 104621-10-5
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: LHOZTQDDNBETIP-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±37.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1,3-二乙基-2-甲基-5-硝基-1H-吲哚 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成 1,3-diethyl-N,N,2-trimethylindol-5-amine
  参考文献：
  名称：

  2,3-Dialkyl(dimethylamino)indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors

  摘要：

  2,3-Dialkyl(dimethylamino)indoles, synthesized via the Fisher indole synthesis, were found to weakly bind to 5HT1 and 5HT2 sites in brain cortical membranes (IC50 greater than 1 microM at both sites for all compounds). These (dimethylamino)indoles were relatively potent antagonists of the serotonin receptor in the rat stomach fundus. At higher concentrations, several of the compounds were weak agonists at this receptor. For direct comparison with data obtained in the isolated rat fundus, antagonism of serotonin-induced contractions at 5HT2 receptors in the rat jugular vein was also examined. Several of the compounds showed good selectivity for the fundus receptor relative to the 5HT2 receptor; together with minimal affinity for 5HT1 and 5HT2 binding sites in brain cortical membranes, these results support the idea that the serotonin receptor in the stomach fundus is distinct from 5HT1 and 5HT2 binding sites.

  DOI：

  10.1021/jm00161a048
• 作为产物：
  描述：

  2-戊酮(对硝基苯基)腙 在 盐酸 、 sodium hydride 作用下， 反应 2.5h， 生成 1,3-二乙基-2-甲基-5-硝基-1H-吲哚
  参考文献：
  名称：

  2,3-Dialkyl(dimethylamino)indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors

  摘要：

  2,3-Dialkyl(dimethylamino)indoles, synthesized via the Fisher indole synthesis, were found to weakly bind to 5HT1 and 5HT2 sites in brain cortical membranes (IC50 greater than 1 microM at both sites for all compounds). These (dimethylamino)indoles were relatively potent antagonists of the serotonin receptor in the rat stomach fundus. At higher concentrations, several of the compounds were weak agonists at this receptor. For direct comparison with data obtained in the isolated rat fundus, antagonism of serotonin-induced contractions at 5HT2 receptors in the rat jugular vein was also examined. Several of the compounds showed good selectivity for the fundus receptor relative to the 5HT2 receptor; together with minimal affinity for 5HT1 and 5HT2 binding sites in brain cortical membranes, these results support the idea that the serotonin receptor in the stomach fundus is distinct from 5HT1 and 5HT2 binding sites.

  DOI：

  10.1021/jm00161a048

文献信息

• INDOLE UREAS AS 5 HT RECEPTOR ANTAGONIST
  申请人：Beecham Group p.l.c.

  公开号：EP0550507A1

  公开（公告）日：1993-07-14
• US5328922A
  申请人：——

  公开号：US5328922A

  公开（公告）日：1994-07-12
• [EN] INDOLE UREAS AS 5 HT RECEPTOR ANTAGONIST
  申请人：——

  公开号：WO1992005170A1

  公开（公告）日：1992-04-02

  [EN] Indole ureas, pharmaceutical compositions containing them and processes for their preparation.
  [FR] Urées d'indole, compositions pharmaceutiques les contenant et leurs procédés de préparation.
• 2,3-Dialkyl(dimethylamino)indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors
  作者：Pawel Fludzinski、Laura A. Wittenauer、Kathryn W. Schenck、Marlene L. Cohen

  DOI：10.1021/jm00161a048

  日期：1986.11

  2,3-Dialkyl(dimethylamino)indoles, synthesized via the Fisher indole synthesis, were found to weakly bind to 5HT1 and 5HT2 sites in brain cortical membranes (IC50 greater than 1 microM at both sites for all compounds). These (dimethylamino)indoles were relatively potent antagonists of the serotonin receptor in the rat stomach fundus. At higher concentrations, several of the compounds were weak agonists at this receptor. For direct comparison with data obtained in the isolated rat fundus, antagonism of serotonin-induced contractions at 5HT2 receptors in the rat jugular vein was also examined. Several of the compounds showed good selectivity for the fundus receptor relative to the 5HT2 receptor; together with minimal affinity for 5HT1 and 5HT2 binding sites in brain cortical membranes, these results support the idea that the serotonin receptor in the stomach fundus is distinct from 5HT1 and 5HT2 binding sites.