1H-吡咯并[3,2-c]吡啶-3-乙胺 | 1778-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 1H-吡咯并[3,2-c]吡啶-3-乙胺
• 中文别名: 2,6-二乙基苯酚
• 英文名称: 3-aminoethyl-1H-pyrrolo[3,2-c]pyridine
• 英文别名: 2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine；5-azatryptamine；3-(β-Aminoethyl)-5-azaindol；2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethylamine
• CAS: 1778-74-1
• 化学式: C₉H₁₁N₃
• 分子量: 161.206
• InChiKey: MPGWXKYGIDJLQT-UHFFFAOYSA-N

物化性质

• 沸点：
  376.0±27.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  1H-吡咯并[3,2-c]吡啶-3-乙胺 在 羟胺 、 sodium methylate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成 (E)-N-hydroxy-3-(4-{[2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethylamino]methyl}phenyl)acrylamide
  参考文献：
  名称：

  Optimization of the in Vitro Cardiac Safety of Hydroxamate-Based Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent. HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree, of pharmacophore homology between these two targets was discovered. This, similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homology model, two compounds, 11r and 25i, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

  DOI：

  10.1021/jm200388e
• 作为产物：
  描述：

  5-氮杂吲哚 在 ammonium hydroxide 、 Rh/Al₂O₃ 、 氢气 、 硫酸二甲酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 正丁醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.5h， 生成 1H-吡咯并[3,2-c]吡啶-3-乙胺
  参考文献：
  名称：

  Optimization of the in Vitro Cardiac Safety of Hydroxamate-Based Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent. HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree, of pharmacophore homology between these two targets was discovered. This, similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homology model, two compounds, 11r and 25i, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

  DOI：

  10.1021/jm200388e

文献信息

• Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands
  申请人：Wyeth

  公开号：US20030171395A1

  公开（公告）日：2003-09-11

  The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of disorders relating to or affected by the 5-HT6 receptor. 1

  本发明提供了一种I式化合物及其用于治疗与5-HT6受体相关或受其影响的疾病的用途。
• AZAINDOLYLALKYLAMINE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS
  申请人：BERNOTAS Ronald Charles

  公开号：US20080114023A1

  公开（公告）日：2008-05-15

  The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of disorders relating to or affected by the 5-HT6 receptor.

  本发明提供一种公式I的化合物以及其在治疗与或受5-HT6受体影响的疾病方面的应用。
• 5-ZATRYPTAMINE ANALOGS AS h5-HT6 SEROTONIN RECEPTOR LIGANDS
  作者：Manik Pullagurla、Małgorzata Dukat、Bryan L. Roth、Vincent Setola、Richard A. Glennon

  DOI：10.1007/s00044-004-0121-8

  日期：2005.1

  5-Aza analogs were prepared of several tryptamine derivatives and a skatole derivative known to bind at human 5-HT6 receptors and evaluated to determine if they bind in a manner similar to their indolic analogs. In general, the azatryptamines did not behave exactly like their tryptamine counterparts, but the behavior of NI-benzenesulfonyl analogs was reminiscent of the known arylsulfonyltryptamines. For example, N-1-(4-aminobenzenesulfonyl)-5-azaskatole (18; K-i = 41 nM) displayed an affinity comparable to N-1-(4-aminobenzenesulfonyl)skatole.
• [EN] INDOLE AHR INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS D'INDOLE AHR ET LEURS UTILISATIONS
  申请人：KYN THERAPEUTICS

  公开号：WO2018195397A3

  公开（公告）日：2018-12-13
• US6800640B2
  申请人：——

  公开号：US6800640B2

  公开（公告）日：2004-10-05