6,8-dimethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 31601-86-2

• 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: 6,8-dimethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6,8-Dimethyl-4-oxo-1,4-dihydro-chinolin-3-carbonsaeure；6,8-Dimethyl-4-hydroxyquinoline-3-carboxylic acid；6,8-dimethyl-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 31601-86-2
• 化学式: C₁₂H₁₁NO₃
• mdl: MFCD02081545
• 分子量: 217.224
• InChiKey: IZUOQXWRSVPGRM-UHFFFAOYSA-N

物化性质

• 沸点：
  396.5±42.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  6,8-dimethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 反应 1.0h， 生成 6,8-dimethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Evaluation of 3-Carboxy-4(1H)-quinolones as Inhibitors of Human Protein Kinase CK2

  摘要：

  Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitorss3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC50 = 0.3 mu M) and 4-oxo-1,4-dihydrobenzo[h] quinoline-3-carboxylic acid (9) (IC50 = 1 AM), are ATP competitive (K-i values are 0.06 and 0.28 mu M, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.

  DOI：

  10.1021/jm050048t