7-(3-amino-1H-indazol-4-yl)-N-phenyl-2H-benzo[b][1,4]oxazine-4(3H)-carboxamide | 1571111-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-(3-amino-1H-indazol-4-yl)-N-phenyl-2H-benzo[b][1,4]oxazine-4(3H)-carboxamide
• 英文别名: 7-(3-amino-1H-indazol-4-yl)-N-phenyl-2,3-dihydro-1,4-benzoxazine-4-carboxamide
• CAS: 1571111-32-4
• 化学式: C₂₂H₁₉N₅O₂
• 分子量: 385.425
• InChiKey: DZTDIEVKRWPYNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  96.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-硝基-5-溴苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1'-双(二苯基膦)二茂铁 、 硼烷四氢呋喃络合物 、 potassium acetate 、 铁粉 、 sodium carbonate 、 氯化铵 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 11.5h， 生成 7-(3-amino-1H-indazol-4-yl)-N-phenyl-2H-benzo[b][1,4]oxazine-4(3H)-carboxamide
  参考文献：
  名称：

  Discovery of a New Series of Naphthamides as Potent VEGFR-2 Kinase Inhibitors

  摘要：

  Inhibition of VEGFR-2 signaling pathway has already become one of the most promising approaches for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of a new series of naphthamides as potent inhibitors of VEGFR-2. Among these compounds, 14c exhibited high VEGFR-2 inhibitory potency in both enzymatic and HUVEC cellular proliferation assays, with IC50 values of 1.5 and 0.9 nM, respectively. Kinase selectivity profiling revealed that 14c was a multitargeted inhibitor, and it also exhibited good potency against VEGFR-1, PDGFR-beta, and RET. Furthermore, 14c effectively blocked tube formation of HUVEC at nanomolar level. Overall, 14c might be a promising candidate for the treatment of cancer.

  DOI：

  10.1021/ml5000417

文献信息

• Discovery of a New Series of Naphthamides as Potent VEGFR-2 Kinase Inhibitors
  作者：Yongcong Lv、Mengyuan Li、Ting Liu、Linjiang Tong、Ting Peng、Lixin Wei、Jian Ding、Hua Xie、Wenhu Duan

  DOI：10.1021/ml5000417

  日期：2014.5.8

  Inhibition of VEGFR-2 signaling pathway has already become one of the most promising approaches for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of a new series of naphthamides as potent inhibitors of VEGFR-2. Among these compounds, 14c exhibited high VEGFR-2 inhibitory potency in both enzymatic and HUVEC cellular proliferation assays, with IC50 values of 1.5 and 0.9 nM, respectively. Kinase selectivity profiling revealed that 14c was a multitargeted inhibitor, and it also exhibited good potency against VEGFR-1, PDGFR-beta, and RET. Furthermore, 14c effectively blocked tube formation of HUVEC at nanomolar level. Overall, 14c might be a promising candidate for the treatment of cancer.