8-hydroxy-2-[2-(4-hydroxyphenyl)ethenyl]quinoline-7-carboxylic acid | 281207-49-6

• 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: 8-hydroxy-2-[2-(4-hydroxyphenyl)ethenyl]quinoline-7-carboxylic acid
• CAS: 281207-49-6
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: DXDQPFWGDWVGIG-UHFFFAOYSA-N

物化性质

• 沸点：
  544.7±50.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.65
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  8-羟基-2-甲基喹啉-7-羧酸 、 对羟基苯甲醛 在 乙酸酐 、 吡啶 作用下， 以 水 为溶剂， 生成 8-hydroxy-2-[2-(4-hydroxyphenyl)ethenyl]quinoline-7-carboxylic acid
  参考文献：
  名称：

  Identification and structure–activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase

  摘要：

  Pim-1 kinase is a cytoplasmic serine/threonine kinase that controls programmed cell death by phosphorylating substrates that regulate both apotosis and cellular metabolism. A series of 2-styrylquinolines and quinoline-2-carboxamides has been identified as potent inhibitors of the Pim-1 kinase. The 8-hydroxyquinoline 7-carboxylic acid moiety appeared to be a crucial pharmacophore for activity. Molecular modeling indicated that interaction of this scaffold with Asp186 and Lys67 residues within the ATP-binding pocket might be responsible for the kinase inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.061