5,7-dichloro-N-(3,4-dihydroxybenzyl)-8-hydroxyquinoline-2-carboxamide | 1227464-52-9

• 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: 5,7-dichloro-N-(3,4-dihydroxybenzyl)-8-hydroxyquinoline-2-carboxamide
• 英文别名: 5,7-dichloro-N-[(3,4-dihydroxyphenyl)methyl]-8-hydroxyquinoline-2-carboxamide
• CAS: 1227464-52-9
• 化学式: C₁₇H₁₂Cl₂N₂O₄
• 分子量: 379.199
• InChiKey: RTIAMATWOMLIHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 生成 5,7-dichloro-N-(3,4-dihydroxybenzyl)-8-hydroxyquinoline-2-carboxamide
  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