8-hydroxy-4-oxo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

• 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: 8-hydroxy-4-oxo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
• 英文别名: 3-hydroxykynurenine yellow；Quinaldic acid, 1,2,3,4-tetrahydro-8-hydroxy-4-oxo-, L-；8-hydroxy-4-oxo-2,3-dihydro-1H-quinoline-2-carboxylic acid
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: CWRGBKGETXFNQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  DL-3-羟基犬尿氨酸 在 碳酸氢钠 作用下， 反应 24.0h， 以22%的产率得到8-hydroxy-4-oxo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
  参考文献：
  名称：

  Novel human lens metabolites from normal and cataractous human lenses

  摘要：

  4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.133

文献信息

• Tetrahydroquinoline derivatives useful for neurodegenerative disorders
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0386839B1

  公开（公告）日：1997-01-15
• US5231102A
  申请人：——

  公开号：US5231102A

  公开（公告）日：1993-07-27
• Novel human lens metabolites from normal and cataractous human lenses
  作者：Jasminka Mizdrak、Peter G. Hains、Danuta Kalinowski、Roger J.W. Truscott、Michael J. Davies、Joanne F. Jamie

  DOI：10.1016/j.tet.2007.03.133

  日期：2007.6

  4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses. (c) 2007 Elsevier Ltd. All rights reserved.