5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid | 130064-06-1

• 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: 5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid
• 英文别名: 5,7-dibromokynurenic acid；5,7-dibromo-4-oxo-1H-quinoline-2-carboxylic acid
• CAS: 130064-06-1
• 化学式: C₁₀H₅Br₂NO₃
• 分子量: 346.963
• InChiKey: QQKJUYOEHGDJPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid 在 copper(l) iodide 、 tin (II) sulfate 、 2,5-二羟基苯甲酸 、 柠檬酸 作用下， 生成 5-bromo-7-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of [77Br] 5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid, a possible SPECT tracer for NMDA receptor studies

  摘要：

  The synthesis of [Br-77] 5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid is described. The labelling is performed in order to obtain a tracer for SPECT studies of the N-methyl-D-aspartate receptor in human brain. Radiosynthesis was carried out using a non-isotopic nucleophilic halogen exchange, starting from 5-iodo-7-bromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid. In order to obtain the best radiochemical yield, several parameters such as reaction temperature, reaction time, amount of precursor and amount of Cu catalyst were studied. Under the best labelling conditions, the radiochemical yield was 85 %. The product was found to be chemically and radiochemically pure as determined by HPLC.

  DOI：

  10.1002/(sici)1099-1344(199609)38:9<795::aid-jlcr891>3.0.co;2-2
• 作为产物：
  描述：

  2,6-二溴-4-硝基苯胺 在 盐酸 、 sodium hydroxide 、 硫酸 、 铁粉 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 二苯醚 、 乙醇 为溶剂， 反应 16.25h， 生成 5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid
  参考文献：
  名称：

  Dumont, Filip; Slegers, Guido, Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 8, p. 505 - 508

  摘要：

  DOI：

文献信息

• Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0303387A1

  公开（公告）日：1989-02-15

  4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-­aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-­acidic group or a group convertible thereto in vivo, other than carboxy or C₁₋₆ alkoxycarbonyl, are novel compounds, as also are compounds of formula II wherein R² represents carboxy or a group convertible thereto in vivo, R⁶ is hydrogen and R⁵ and R⁷ represent C₁₋₆ alkyl or halogen, provided that R⁵ and R⁷ are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.

  具有 2-酸性基团或体内可转化基团的 4-氧代-1,4-二氢喹啉化合物及其药学上可接受的盐类是 N-甲基-D-天冬氨酸（NMDA）受体的强效特异性拮抗剂，因此可用于治疗神经退行性疾病。除羧基或 C₁₋₆ 烷氧羰基外，具有 2-酸性基团或在体内可转化的基团的 4-氧代-1,4-二氢喹啉化合物是新型化合物，如式 II 所示的化合物 其中 R² 代表羧基或体内可转化为羧基的基团，R⁶ 是氢，R⁵ 和 R⁷ 代表 C₁₋₆ 烷基或卤素，但 R⁵ 和 R⁷ 不能同时为氯或同时为溴。
• US5270309A
  申请人：——

  公开号：US5270309A

  公开（公告）日：1993-12-14
• Dumont, Filip; Slegers, Guido, Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 8, p. 505 - 508
  作者：Dumont, Filip、Slegers, Guido

  DOI：——

  日期：——
• Synthesis of [77Br] 5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid, a possible SPECT tracer for NMDA receptor studies
  作者：F. Dumont、G. Slegers

  DOI：10.1002/(sici)1099-1344(199609)38:9<795::aid-jlcr891>3.0.co;2-2

  日期：1996.9

  The synthesis of [Br-77] 5,7-dibromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid is described. The labelling is performed in order to obtain a tracer for SPECT studies of the N-methyl-D-aspartate receptor in human brain. Radiosynthesis was carried out using a non-isotopic nucleophilic halogen exchange, starting from 5-iodo-7-bromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid. In order to obtain the best radiochemical yield, several parameters such as reaction temperature, reaction time, amount of precursor and amount of Cu catalyst were studied. Under the best labelling conditions, the radiochemical yield was 85 %. The product was found to be chemically and radiochemically pure as determined by HPLC.