5-bromo-N-(quinolin-3-yl)nicotinamide | 313562-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-bromo-N-(quinolin-3-yl)nicotinamide
• 英文别名: 5-bromo-N-quinolin-3-ylpyridine-3-carboxamide
• CAS: 313562-06-0
• 化学式: C₁₅H₁₀BrN₃O
• 分子量: 328.168
• InChiKey: FXZHYEKBAMZBOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基喹啉 、 5-溴烟酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以67%的产率得到5-bromo-N-(quinolin-3-yl)nicotinamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of quinoline amide derivatives as novel VEGFR-2 inhibitors

  摘要：

  Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in the process of cancer angiogenesis. A series of quinoline amide derivatives were prepared and found to be good inhibitors of VEGFR-2. The inhibitory activities were investigated against VEGFR-2 kinase and human umbilical vein endothelial cells (HUVEC) in vitro. Compound 6 (5-chloro-2-hydroxy-N-(quinolin-8-yl)benzamide) exhibited the most potent inhibitory activity (IC(50) = 3.8 and 5.5 nM for VEGFR-2 kinase and HUVEC, respectively). Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of VEGFR-2, which demonstrates that compound 6 is a potential agent for cancer therapy deserving further researching. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.014

文献信息

• Design, synthesis and biological evaluation of quinoline amide derivatives as novel VEGFR-2 inhibitors
  作者：Ying Yang、Lei Shi、Yang Zhou、Huan-Qiu Li、Zhen-Wei Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2010.09.014

  日期：2010.11

  Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in the process of cancer angiogenesis. A series of quinoline amide derivatives were prepared and found to be good inhibitors of VEGFR-2. The inhibitory activities were investigated against VEGFR-2 kinase and human umbilical vein endothelial cells (HUVEC) in vitro. Compound 6 (5-chloro-2-hydroxy-N-(quinolin-8-yl)benzamide) exhibited the most potent inhibitory activity (IC(50) = 3.8 and 5.5 nM for VEGFR-2 kinase and HUVEC, respectively). Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of VEGFR-2, which demonstrates that compound 6 is a potential agent for cancer therapy deserving further researching. (C) 2010 Elsevier Ltd. All rights reserved.