N-[5-(2-aminoquinazolin-6-yl)pyridin-3-yl]benzenesulfonamide | 1351597-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[5-(2-aminoquinazolin-6-yl)pyridin-3-yl]benzenesulfonamide
• CAS: 1351597-73-3
• 化学式: C₁₉H₁₅N₅O₂S
• 分子量: 377.426
• InChiKey: CHQIIDGJJHNJCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-溴-3-氨基吡啶 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 N-[5-(2-aminoquinazolin-6-yl)pyridin-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Discovery of new aminopyrimidine-based phosphoinositide 3-kinase beta (PI3Kβ) inhibitors with selectivity over PI3Kα

  摘要：

  Phosphatidylinositol-3-kinase beta (PI3K beta) is an important therapeutic target in arterial thrombosis and special types of cancer. In this study, a new series of aminopyridine-based PI3K beta selective inhibitors have been developed by the structure-based design strategy. When incorporated with the phenyl ring on sulfonamide moiety, aminopyrimidine analogs showed good potency on PI3K beta and selectivity over PI3K alpha. Intriguingly, replacement of phenyl group on sulfonamide with naphthyl group enhanced selectivity over PI3K alpha while retaining submicromolar PI3K beta potency. Molecular modeling suggests that increased PI3K beta specificity is caused by the interaction with salt bridge (Lys782-Asp923) and Asp862 that creat a unique pocket in PI3K beta. These results clearly provide useful insight in the design of new PI3K beta inhibitors with high potency and selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.118