4-羟基-5,8-二甲基喹啉-3-羧酸乙酯 | 303009-95-2

• 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
• 中文名称: 4-羟基-5,8-二甲基喹啉-3-羧酸乙酯
• 中文别名: 乙基-4-羟基-5,8-二甲基-3-喹啉；54-羟基-3,8-二甲基喹啉-3-羧酸乙酯；54-羟基-3,8-二甲基喹啉-3-羧酸乙酯，5,8-二甲基-4-羟基喹啉-3-羧酸乙酯
• 英文名称: 4-Hydroxy-5,8-dimethylquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5,8-dimethyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 303009-95-2
• 化学式: C₁₄H₁₅NO₃
• mdl: MFCD05742466
• 分子量: 245.278
• InChiKey: HMUSWIYPMAPVDO-UHFFFAOYSA-N

物化性质

• 沸点：
  367.7±37.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基-5,8-二甲基喹啉-3-羧酸乙酯 在 sodium hydroxide 作用下， 反应 1.0h， 生成 5,8-二甲基-4-羟基喹啉-3-羧酸
  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
• 作为产物：
  描述：

  2,5-二甲基苯胺 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 4-羟基-5,8-二甲基喹啉-3-羧酸乙酯
  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

文献信息

• [EN] PROCESS FOR PREPARING MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR<br/>[FR] PROCÉDÉ DE PRÉPARATION DE MODULATEURS DE RÉGULATEUR DE CONDUCTANCE TRANSMEMBRANAIRE DE FIBROSE KYSTIQUE
  申请人：VERTEX PHARMA

  公开号：WO2011050215A1

  公开（公告）日：2011-04-28

  The present invention relates to processes for preparing solid state forms of N-(4-(7-azabicyclo[2.2. 1]heptan-7-yl)-2-(trifluoromethyl)phenyl)-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide, including Compound 1 Form A, Compound 1 Form A- HCl, Compound 1 Form B, and Compound 1 Form B-HCl, any combination of these forms, pharmaceutical compositions thereof, and methods of treatment therewith.

  本发明涉及制备N-(4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(三氟甲基)苯基)-4-氧代-5-(三氟甲基)-1,4-二氢喹啉-3-羧酰胺的固态形式的方法，包括化合物1A型，化合物1A型-HCl，化合物1B型和化合物1B型-HCl，这些形式的任意组合，其制备的制药组合物以及使用这些组合物的治疗方法。
• Evaluation of 3-Carboxy-4(1<i>H</i>)-quinolones as Inhibitors of Human Protein Kinase CK2
  作者：Andriy G. Golub、Olexander Ya. Yakovenko、Volodymyr G. Bdzhola、Vladislav M. Sapelkin、Piotr Zien、Sergiy M. Yarmoluk

  DOI：10.1021/jm050048t

  日期：2006.11.1

  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.