5-(2-(dimethylamino)ethoxy)-1H-indole | 1026598-91-3

• 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-(2-(dimethylamino)ethoxy)-1H-indole
• 英文别名: 5-(2-dimethylamino-ethoxy)-1H-indol；5-[2-(dimethylamino)ethoxy]indol；5-(2-dimethylaminoethoxy)indole；2-(1H-indol-5-yloxy)-N,N-dimethylethanamine
• CAS: 1026598-91-3
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: BXQZUQSMJSNKBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-(dimethylamino)ethoxy)-1H-indole 在 盐酸 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 6.75h， 生成 1-[(E)-[5-[2-(dimethylamino)ethoxy]-1H-indol-3-yl]methylideneamino]-2-pentylguanidine
  参考文献：
  名称：

  The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists

  摘要：

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.

  DOI：

  10.1021/jm00013a010
• 作为产物：
  描述：

  4-硝基间甲苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 镍 potassium carbonate 、 一水合肼 作用下， 以 丙酮 为溶剂， 反应 8.5h， 生成 5-(2-(dimethylamino)ethoxy)-1H-indole
  参考文献：
  名称：

  The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists

  摘要：

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.

  DOI：

  10.1021/jm00013a010

文献信息

• SECO-CYCLOPROPAPYRROLOINDOLE COMPOUNDS, ANTIBODY-DRUG CONJUGATES THEREOF, AND METHODS OF MAKING AND USE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20180051031A1

  公开（公告）日：2018-02-22

  seco-Cyclopropapyrroloindole compounds of formula (I) where Hal, R 1 , R 2 , and R 3 are as defined in the application, are potent anti-cancer agents that can be used in antibody-drug conjugates.
• [DE] FLUORESZENZFARBSTOFFE<br/>[EN] FLUORESCENCE DYES<br/>[FR] COLORANTS FLUORESCENTS
  申请人：GEORG AUGUST UNI GOETTINGEN STIFTUNG OEFFENLICHEN RECHTS

  公开号：WO2011051484A1

  公开（公告）日：2011-05-05

  Die vorliegende Erfindung betrifft neue, als Fluoreszenzfarbstoffe geeignete Verbindungen. Insbesondere betrifft die vorliegende Erfindung eine neue Klasse von mit Chromophoren derivatisierten, pharmakologisch aktiven Verbindungen. In einem weiteren Aspekt richtet sich die vorliegende Erfindung auf Anwendungen der erfindungsgemäßen Verbindungen.
• The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists
  作者：Karl-Heinz Buchheit、Rainer Gamse、Rudolf Giger、Daniel Hoyer、Francois Klein、Edgar Kloeppner、Hans-Juergen Pfannkuche、Henri Mattes

  DOI：10.1021/jm00013a010

  日期：1995.6

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.