4-hydroxy-6-phenoxy-quinoline-3-carboxylic acid | 35975-94-1

• 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-phenoxy-quinoline-3-carboxylic acid
• 英文别名: 4-Hydroxy-6-phenoxy-chinolin-3-carbonsaeure；4-Oxo-6-phenoxy-1,4-dihydroquinoline-3-carboxylic acid；4-oxo-6-phenoxy-1H-quinoline-3-carboxylic acid
• CAS: 35975-94-1
• 化学式: C₁₆H₁₁NO₄
• mdl: MFCD05744847
• 分子量: 281.268
• InChiKey: NTPGNGGZYMRORF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-phenoxy-quinoline-3-carboxylic acid 在 三氯氧磷 作用下， 生成 4-chloro-6-phenoxy-quinoline
  参考文献：
  名称：

  用乙氧基亚甲基丙二酸酯法合成一些4-喹啉醇和4-氯喹啉。

  摘要：

  DOI：

  10.1021/ja01211a038
• 作为产物：
  描述：

  4-氨基二苯醚 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 4-hydroxy-6-phenoxy-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Preparation of Quinoline Hexose Analogs as Novel Chloroquine-Resistant Malaria Treatments (1). Synthesis of 4-Hydroxyquinoline-.BETA.-glucosides

  摘要：

  喹啉己糖类似物有望成为治疗耐氯喹疟疾的新型药物。在此，我们报告了通过 4 个步骤从苯胺制备 4-羟基喹啉-β-葡萄糖苷的过程。

  DOI：

  10.1248/cpb.55.821

文献信息

• 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.
• WO2008/117079
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ANTIMICROBIAL COMPOUNDS BASED UPON 4-AMINOQUINOLINE<br/>[FR] COMPOSÉS ANTIMICROBIENS À BASE DE 4-AMINOQUINOLÉINE
  申请人：HELPERBY THERAPEUTICS LTD

  公开号：WO2008117079A1

  公开（公告）日：2008-10-02

  [EN] There is provided compounds of formula I wherein R¹, R², R³, R⁴, X¹, X² and A have meanings given in the description. Also provided are medical uses of such compounds, such as the killing clinically latent microorganisms or treating microbial infections.
  [FR] L'invention porte sur des composés de formule I dans laquelle R¹, R², R³, R⁴, X¹, X² jusqu'à A ont les significations données dans la description. L'invention porte également sur des utilisations médicales de ces composés, telles que la destruction de micro-organismes cliniquement latents ou le traitement d'infections microbiennes.
• The Synthesis of Some 4-Quinolinols and 4-Chloroquinolines by the Ethoxymethylenemalonic Ester Method¹
  作者：Byron Riegel、Gerald R. Lappin、Bernard H. Adelson、Richard I. Jackson、Charles J. Albisetti、R. M. Dodson、Robert H. Baker

  DOI：10.1021/ja01211a038

  日期：1946.7
• Preparation of Quinoline Hexose Analogs as Novel Chloroquine-Resistant Malaria Treatments (1). Synthesis of 4-Hydroxyquinoline-.BETA.-glucosides
  作者：Hiroshi Suzuki、Nagwa S. M. Aly、Yusuke Wataya、Hye-Sook Kim、Ikumi Tamai、Masaki Kita、Daisuke Uemura

  DOI：10.1248/cpb.55.821

  日期：——

  Quinoline hexose analogs are expected to be useful as novel agents for treatment of chloroquine-resistant malaria. Here, we report preparation of 4-hydroxy quinoline-β-glucosides from anilines in 4 steps.

  喹啉己糖类似物有望成为治疗耐氯喹疟疾的新型药物。在此，我们报告了通过 4 个步骤从苯胺制备 4-羟基喹啉-β-葡萄糖苷的过程。