3-(morpholinosulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-amine | 1261082-91-0

• 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-(morpholinosulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-amine
• 英文别名: 3-(4-morpholinylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine；3-(Morpholinosulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2-amine；3-morpholin-4-ylsulfonyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
• CAS: 1261082-91-0
• 化学式: C₁₅H₂₄BN₃O₅S
• 分子量: 369.25
• InChiKey: OBADVQHUFHMBIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(5-溴-1H-吡咯并[2,3-B]吡啶-3-基)-乙酮 、 3-(morpholinosulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-amine 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 1-(5-(6-amino-5-(morpholinosulfonyl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone
  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

文献信息

• Design and Synthesis of Imidazopyridine Analogues as Inhibitors of Phosphoinositide 3-Kinase Signaling and Angiogenesis
  作者：Okseon Kim、Yujeong Jeong、Hyunseung Lee、Sun-Sun Hong、Sungwoo Hong

  DOI：10.1021/jm101582z

  日期：2011.4.14

  Phosphatidylinositol 3-kinase α (PI3Kα) is an important regulator of intracellular signaling pathways, controlling remarkably diverse arrays of physiological processes. Because the PI3K pathway is frequently up-regulated in human cancers, the inhibition of PI3Kα can be a promising approach to cancer therapy. In this study, we have designed and synthesized a new series of imidazo[1,2-a]pyridine derivatives

  磷脂酰肌醇3-激酶α（PI3Kα）是细胞内信号通路的重要调节剂，可控制多种多样的生理过程。由于PI3K途径在人类癌症中经常被上调，因此PI3Kα的抑制可能是一种有前途的癌症治疗方法。在本研究中，我们通过片段增长策略设计并合成了一系列新的咪唑并[1,2- a ]吡啶衍生物作为PI3Kα抑制剂。通过改变咪唑[1,2- a]的3和6位上的基团]吡啶，我们研究了结构活性关系（SAR）谱，并鉴定了一系列有效的PI3Kα抑制剂。代表性衍生物在细胞增殖和凋亡测定中显示出良好的活性。而且，这些抑制剂表现出值得注意的抗血管生成活性。
• [EN] BENZIMIDAZOLE DERIVATIVES AS ANTIVIRAL AGENTS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE EN TANT QU'AGENTS ANTIVIRAUX
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012174312A3

  公开（公告）日：2013-02-28
• 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.