1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxylic acid | 254993-48-1

• 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: 1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxylic acid
• 英文别名: 4-Hydroxy-1-methyl-5-methylsulfanyl-2-oxoquinoline-3-carboxylic acid
• CAS: 254993-48-1
• 化学式: C₁₂H₁₁NO₄S
• 分子量: 265.29
• InChiKey: UIWPRIXDMUBIOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-三氟甲基-N-甲基苯胺 、 1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到N-methyl-N-(4-trifluoromethyl-phenyl)-1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxamide
  参考文献：
  名称：

  QUINOLINE DERIVATIVES

  摘要：

  公开号：

  EP1097139B1
• 作为产物：
  描述：

  ethyl 4-amino-1,2-dihydro-1-methyl-5-methylthio-2-oxo-3-quinolinecarboxylate 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship

  摘要：

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

  DOI：

  10.1021/jm031044w