3-(5-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzonitrile | 1377503-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(5-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzonitrile
• 英文别名: 3-[5-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]benzonitrile
• CAS: 1377503-50-8
• 化学式: C₂₀H₁₄N₄
• 分子量: 310.358
• InChiKey: IPYLXIRSDAUFJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氰基苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 3-(5-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzonitrile
  参考文献：
  名称：

  Structure-based de novo design and identification of D816V mutant-selective c-KIT inhibitors

  摘要：

  通过使用改进的精确溶剂自由能的评分函数进行基于结构的全新设计，确定了具有纳摩尔抑制活性和对功能获得性D816V突变体高选择性的新型7-氮杂吲哚基c-KIT抑制剂。

  DOI：

  10.1039/c4ob00053f

文献信息

• Design, Synthesis, and Evaluation of 3,5-Disubstituted 7-Azaindoles as Trk Inhibitors with Anticancer and Antiangiogenic Activities
  作者：Seunghee Hong、Jinhee Kim、Ju Hyeon Seo、Kyung Hee Jung、Soon-Sun Hong、Sungwoo Hong

  DOI：10.1021/jm3002982

  日期：2012.6.14

  Tropomyosin-related kinase A (TrkA) is considered a promising target in the development of a therapeutic treatment of cancer and pain. In this study, we designed and synthesized a series of novel 7-azaindole-based Trk kinase inhibitors through the structure-based design strategy. By varying the functional groups at the 3 and 5 positions of a 7-azaindole scaffold, we studied the structure-activity relationships (SAR) profiles and identified a series of potent Trk inhibitors. Representative derivatives showed desirable activity in cellular proliferation and apoptosis assays. Moreover, these inhibitors exhibited noteworthy antiangiogenic activity.
• Structure-based de novo design and identification of D816V mutant-selective c-KIT inhibitors
  作者：Hwangseo Park、Soyoung Lee、Suhyun Lee、Sungwoo Hong

  DOI：10.1039/c4ob00053f

  日期：——

  New 7-azaindole-based c-KIT inhibitors with nanomolar inhibitory activity and high selectivity for the gain-of-function D816V mutant were identified through the structure-based de novo design using the scoring function improved by implementing an accurate solvation free energy.

  通过使用改进的精确溶剂自由能的评分函数进行基于结构的全新设计，确定了具有纳摩尔抑制活性和对功能获得性D816V突变体高选择性的新型7-氮杂吲哚基c-KIT抑制剂。