N-(3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanesulfonamide | 1261082-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanesulfonamide
• 英文别名: N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl]methanesulfonamide
• CAS: 1261082-89-6
• 化学式: C₁₄H₁₂BrN₃O₂S
• 分子量: 366.238
• InChiKey: WDFSKKRMRKRSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基吡啶-5-硼酸 、 N-(3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanesulfonamide 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， 生成
  参考文献：
  名称：

  Discovery of new azaindole-based PI3Kα inhibitors: Apoptotic and antiangiogenic effect on cancer cells

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.10.108
• 作为产物：
  描述：

  3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)aniline 、 甲基磺酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以68.2%的产率得到N-(3-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanesulfonamide
  参考文献：
  名称：

  Discovery of new azaindole-based PI3Kα inhibitors: Apoptotic and antiangiogenic effect on cancer cells

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.10.108