4-氧代-1H-喹啉-3,7-二羧酸 | 63463-25-2

• 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-氧代-1H-喹啉-3,7-二羧酸
• 英文名称: 4-Hydroxy-quinoline-3,7-dicarboxylic acid
• 英文别名: 4-oxo-1H-quinoline-3,7-dicarboxylic acid
• CAS: 63463-25-2
• 化学式: C₁₁H₇NO₅
• mdl: MFCD12401933
• 分子量: 233.18
• InChiKey: QLHSVJRXHWXBHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[[(E)-2-carboxy-3-ethoxy-3-oxoprop-1-enyl]amino]benzoic acid 以84%的产率得到
  参考文献：
  名称：

  Bueyuekbingoel Erdem, Das Net, Klopman Gilles, Arch. Pharm., 327 (1994) N 3, S 129-131

  摘要：

  DOI：

文献信息

• The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids
  作者：Biswadip Banerji、Ana Conejo-Garcia、Luke A. McNeill、Michael A. McDonough、Matthew R. G. Buck、Kirsty S. Hewitson、Neil J. Oldham、Christopher J. Schofield

  DOI：10.1039/b510707e

  日期：——

  Cyclic β-oxocarboxylic acids inhibit factor inhibiting hypoxia-inducible factor via ligation to the active site iron.

  环状β-氧羰基酸通过结合到活性位点铁而抑制缺氧诱导因子抑制因子。
• Synthesis of 1,4-Dihydro-4-oxo-quinoline-3-carboxylic Acid Derivatives as Inhibitors of Rat Lens Aldose Reductase
  作者：Erdem Büyükbingöl、Net Daş、Gilles Klopman

  DOI：10.1002/ardp.19943270302

  日期：——

  The title compounds were prepared according to Scheme 2 and tested as inhibitors of the aldose reductase of rat lens.

  根据方案2制备标题化合物并作为大鼠晶状体醛糖还原酶的抑制剂进行测试。
• 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.
• A Small-Molecule Inhibitor of Nipah Virus Envelope Protein-Mediated Membrane Fusion
  作者：Sabine Niedermeier、Katrin Singethan、Sebastian G. Rohrer、Magnus Matz、Markus Kossner、Sandra Diederich、Andrea Maisner、Jens Schmitz、Georg Hiltensperger、Knut Baumann、Ulrike Holzgrabe、Jürgen Schneider-Schaulies

  DOI：10.1021/jm900411s

  日期：2009.7.23

  Nipah virus (NiV), a highly pathogenic paramyxovirus. causes respiratory disease in pigs and severe febrile encephalitis in humans with high mortality rates. On the basis of the structural similarity of viral fusion (F) proteins within the family Paramyxoviridae, we designed and tested 18 quinolone derivatives in a NiV and measles virus (MV) envelope protein-based fusion assay beside evaluation of cytotoxicity. We found five compounds successfully inhibiting NiV envelope protein-induced cell fusion. The most active molecules (19 and 20), which also inhibit the syncytium formation induced by infectious NiV and show a low cytotoxicity in Vero cells, represent a promising lead quinolone-type compound structure. Molecular modeling indicated that compound 19 fits well into a particular protein cavity present on the NiV F protein that is important for the fusion process.
• Bueyuekbingoel Erdem, Das Net, Klopman Gilles, Arch. Pharm., 327 (1994) N 3, S 129-131
  作者：Bueyuekbingoel Erdem, Das Net, Klopman Gilles

  DOI：——

  日期：——