2-methyl-3-ethyl-5-nitroindole | 60676-78-0

• 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: 2-methyl-3-ethyl-5-nitroindole
• 英文别名: 3-ethyl-2-methyl-5-nitro-indole；3-Aethyl-2-methyl-5-nitro-indol；5-Nitro-2-methyl-3-aethyl-indol；3-Ethyl-2-methyl-5-nitro-1h-indole
• CAS: 60676-78-0
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: QMERMWACWLHWSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-ethyl-5-nitroindole 在 sodium hydride 、 N,N-二甲基甲酰胺 、 甲苯 作用下， 生成 1,2-二甲基-3-乙基-5-硝基吲哚
  参考文献：
  名称：

  Serotonin Analogs. The Synthesis of 5-Dimethylaminoindoles

  摘要：

  DOI：

  10.1021/ja01634a071
• 作为产物：
  描述：

  2-戊酮(对硝基苯基)腙 在 盐酸 作用下， 以69%的产率得到2-methyl-3-ethyl-5-nitroindole
  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

• The Synthesis of Nitro- and Aminoindoles Analogous to Serotonin
  作者：Elliott Shaw、D. W. Woolley

  DOI：10.1021/ja01104a029

  日期：1953.4
• Vejdelek, Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 1852,1854
  作者：Vejdelek

  DOI：——

  日期：——
• 311. Indoles. Part II. The preparation and oxidation of the Bz-nitro-2-methyl-3-ethyl-, -2 : 3-diphenyl-, and -2-methyl-3-phenyl-indoles
  作者：K. Schofield、R. S. Theobald

  DOI：10.1039/jr9500001505

  日期：——
• 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