3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)aniline | 1261082-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)aniline
• CAS: 1261082-90-9
• 化学式: C₁₃H₁₀BrN₃
• 分子量: 288.147
• InChiKey: SUKABHWEQSGSDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)aniline 、 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 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以26%的产率得到3-(3-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzonitrile
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of 3,5-Disubstituted 7-Azaindoles as Trk Inhibitors with Anticancer and Antiangiogenic Activities

  摘要：

  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.

  DOI：

  10.1021/jm3002982
• 作为产物：
  描述：

  3-氨基苯硼酸 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-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)aniline
  参考文献：
  名称：

  Development and Biological Evaluation of Potent and Selective c-KIT^D816V Inhibitors

  摘要：

  The c-KIT tyrosine kinase has emerged as a potential therapeutic target for an array of diseases. However, there exists a drug resistance that is caused by mutations in c-KIT; therefore, c-KIT remains as a clinical challenge due to limited effective treatment options for therapies. For example, the acquired activating point mutation D816V significantly impairs the efficacy of targeted cancer therapies. Understanding the mechanisms of drug resistance at the molecular level will aid in designing and developing particular inhibitors with the potential to overcome these resistance mutations. We undertake a structure-based de novo design of 7-azaindole as the molecular core using the modified scoring function. This approach led to an identification of new c-KIT inhibitors over 100-fold specific for the D816V mutant relative to the wild-type c-KIT with nanomolar inhibitory activity. More importantly, these compounds potently inhibit clinically relevant D816V mutations of c-KIT in biochemical and cellular studies.

  DOI：

  10.1021/jm500413g

文献信息

• Discovery of new azaindole-based PI3Kα inhibitors: Apoptotic and antiangiogenic effect on cancer cells
  作者：Seunghee Hong、Soyoung Lee、Bomi Kim、Hyunseung Lee、Soon-Sun Hong、Sungwoo Hong

  DOI：10.1016/j.bmcl.2010.10.108

  日期：2010.12

  Phosphatidylinositol-3-kinase alpha (PI3K alpha) is an important target in cancer due to the deregulation of the PI3K/AKT signaling pathway in many tumors. In this study, we designed [3,5-d]-7-azaindole analogs as PI3K alpha inhibitors through the fragment-growing strategy. By varying groups at the 3,5-positions of azaindole, we developed the SAR (Structure-activity relationship) and identified a series of potent PI3K alpha inhibitors. Representative azaindole derivatives showed activity in a cellular proliferation and apoptosis assays. Moreover, B3 exhibited strong antiangiogenic effects on cancer cells. (C) 2010 Elsevier Ltd. All rights reserved.
• Discovery and identification of a novel PI3K inhibitor with enhanced CDK2 inhibition for the treatment of triple negative breast cancer
  作者：Chengbin Yang、Menghui Wang、Yimin Gong、Mingli Deng、Yun Ling、Qingquan Li、Jianxin Wang、Yaming Zhou

  DOI：10.1016/j.bioorg.2023.106779

  日期：2023.11