6-bromo-3-methoxyquinolin-2(1H)-one | 1434103-22-6

• 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-bromo-3-methoxyquinolin-2(1H)-one
• 英文别名: 6-Bromo-3-methoxyquinolin-2(1H)-one；6-bromo-3-methoxy-1H-quinolin-2-one
• CAS: 1434103-22-6
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: WMHLVJZQRMIVJF-UHFFFAOYSA-N

物化性质

• 沸点：
  444.0±45.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-3-methoxyquinolin-2(1H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以50%的产率得到7-bromo-3-hydroxyquinolin-2(1H)-one
  参考文献：
  名称：

  3-Hydroxyquinolin-2(1H)-ones As Inhibitors of Influenza A Endonuclease

  摘要：

  Several 3-hydroxyquinolin-2(1H)-ones. derivatives were synthesized and evaluated as inhibitors of 2009 pandemic H1N1 influenza A endonuclease. All five of the monobrominated 3-hydroxyquinolin (1H)-2-ones derivatives were synthesized. Suzuki-coupling of p-fluorophenylboronic acid with each of these brominated derivatives provided the respective p-fluorophenyl hydroxyquinolin (1H)-2-ones. In addition to 3-hydroxyquinolin-2 (1H)-one, its 4-methyl, 4-phenyl, 4-methyl-7-(p-fluorophenyl), and 4-phenyl-7-(p-fluorophenyl) derivatives were also synthesized. Comparative studies on their relative activity revealed that both 6- and 7-(p-fluorophenyl)-3- hydroxyquinolin-2(1H)-one are among the more potent inhibitors of H1N1 influenza A endonuclease. An X-ray crystal structure of 7-(p-fluorophenyl)-3-hydroxyquinolin-2(1H)-one complexed to the influenza endonuclease revealed that this molecule chelates to two metal ions at the active site of the enzyme.

  DOI：

  10.1021/ml4001112
• 作为产物：
  描述：

  5-溴靛红 、 三甲基硅烷化重氮甲烷 在 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 以54%的产率得到6-bromo-3-methoxyquinolin-2(1H)-one
  参考文献：
  名称：

  [EN] THERAPEUTIC HYDROXYQUINOLONES
  [FR] HYDROXYQUINOLONES THÉRAPEUTIQUES

  摘要：

  该发明提供了式(I)的化合物及其盐，其中R4-R8具有规范中定义的任何含义，以及包含这些化合物或盐的药物组合物以及其在治疗中的使用方法。这些化合物具有有用的抗病毒特性。

  公开号：

  WO2014074926A1

文献信息

• [EN] THERAPEUTIC HYDROXYQUINOLONES<br/>[FR] HYDROXYQUINOLONES THÉRAPEUTIQUES
  申请人：UNIV RUTGERS

  公开号：WO2014074926A1

  公开（公告）日：2014-05-15

  The invention provides compounds of formula (I) and salts thereof wherein R4-R8 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts and methods for their use in therapy. The compounds have useful antiviral properties.

  该发明提供了式(I)的化合物及其盐，其中R4-R8具有规范中定义的任何含义，以及包含这些化合物或盐的药物组合物以及其在治疗中的使用方法。这些化合物具有有用的抗病毒特性。
• THERAPEUTIC HYDROXYQUINOLONES
  申请人：LAVOIE Edmond J.

  公开号：US20150291531A1

  公开（公告）日：2015-10-15

  The invention provides compounds of formula (I) and salts thereof wherein R 4 -R 8 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts and methods for their use in therapy. The compounds have useful antiviral properties.

  该发明提供了公式(I)的化合物及其盐，其中R4-R8具有规范中定义的任何含义，以及包含该化合物或盐的药物组合物和它们在治疗中的使用方法。这些化合物具有有用的抗病毒特性。
• US9701638B2
  申请人：——

  公开号：US9701638B2

  公开（公告）日：2017-07-11
• 3-Hydroxyquinolin-2(1<i>H</i>)-ones As Inhibitors of Influenza A Endonuclease
  作者：Hye Yeon Sagong、Ajit Parhi、Joseph D. Bauman、Disha Patel、R. S. K. Vijayan、Kalyan Das、Eddy Arnold、Edmond J. LaVoie

  DOI：10.1021/ml4001112

  日期：2013.6.13

  Several 3-hydroxyquinolin-2(1H)-ones. derivatives were synthesized and evaluated as inhibitors of 2009 pandemic H1N1 influenza A endonuclease. All five of the monobrominated 3-hydroxyquinolin (1H)-2-ones derivatives were synthesized. Suzuki-coupling of p-fluorophenylboronic acid with each of these brominated derivatives provided the respective p-fluorophenyl hydroxyquinolin (1H)-2-ones. In addition to 3-hydroxyquinolin-2 (1H)-one, its 4-methyl, 4-phenyl, 4-methyl-7-(p-fluorophenyl), and 4-phenyl-7-(p-fluorophenyl) derivatives were also synthesized. Comparative studies on their relative activity revealed that both 6- and 7-(p-fluorophenyl)-3- hydroxyquinolin-2(1H)-one are among the more potent inhibitors of H1N1 influenza A endonuclease. An X-ray crystal structure of 7-(p-fluorophenyl)-3-hydroxyquinolin-2(1H)-one complexed to the influenza endonuclease revealed that this molecule chelates to two metal ions at the active site of the enzyme.