4-hydroxy-6,8-dimethoxy-quinoline-3-carboxylic acid ethyl ester | 26893-06-1

• 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: 4-hydroxy-6,8-dimethoxy-quinoline-3-carboxylic acid ethyl ester
• 英文别名: 4-Hydroxy-6,8-dimethoxy-chinolin-3-carbonsaeure-aethylester；ethyl 6,8-dimethoxy-4-oxo-1H-quinoline-3-carboxylate
• CAS: 26893-06-1
• 化学式: C₁₄H₁₅NO₅
• mdl: MFCD01610198
• 分子量: 277.277
• InChiKey: QHBNTXBHKHDRNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6,8-dimethoxy-quinoline-3-carboxylic acid ethyl ester 在 乙醇 、 丙酮 、 肼 作用下， 反应 2.0h， 生成 4-hydroxy-6,8-dimethoxy-quinoline-3-carboxylic acid isopropylidenehydrazide
  参考文献：
  名称：

  Popli; Dhar, Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 261

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二甲氧基苯胺 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 4-hydroxy-6,8-dimethoxy-quinoline-3-carboxylic acid ethyl ester
  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

• 4-HYDROXYQUINOLINE-3-CARBOXAMIDES AND HYDRAZIDES AS ANTIVIRAL AGENTS
  申请人：Pharmacia & Upjohn Company LLC

  公开号：EP1042295B1

  公开（公告）日：2005-09-07
• OZEKI KOHJI; ISHIZUKA YASUHIRO; SAWADA MASAHIRO; ICHIKAWA TERU; SATO MAKO+, J. PHARM. SOC. JAP., 107,(1987) N 2, 123-134
  作者：OZEKI KOHJI、 ISHIZUKA YASUHIRO、 SAWADA MASAHIRO、 ICHIKAWA TERU、 SATO MAKO+

  DOI：——

  日期：——
• 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.
• Popli; Dhar, Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 261
  作者：Popli、Dhar

  DOI：——

  日期：——