ethyl 6-ethoxy-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate | 675574-97-7

• 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: ethyl 6-ethoxy-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate
• 英文别名: 3-Quinolinecarboxylic acid,6-ethoxy-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-,ethyl ester；ethyl 6-ethoxy-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxylate
• CAS: 675574-97-7
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: SSUFMXDCABPJCT-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±45.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-ethoxy-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate 在 盐酸 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 10.5h， 生成 6-Ethoxy-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (4-fluoro-phenyl)-methyl-amide
  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
• 作为产物：
  描述：

  甲烷三羧酸三乙酯 、 N-methyl-p-phenetidine 以 二苯醚 为溶剂， 反应 3.0h， 以63%的产率得到ethyl 6-ethoxy-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate
  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

文献信息

• Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship
  作者：Stig Jönsson、Gunnar Andersson、Tomas Fex、Tomas Fristedt、Gunnar Hedlund、Karl Jansson、Lisbeth Abramo、Ingela Fritzson、Olga Pekarski、Anna Runström、Helena Sandin、Ingela Thuvesson、Anders Björk

  DOI：10.1021/jm031044w

  日期：2004.4.1

  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).