1,2-Dihydro-4-hydroxy-5-trifluoromethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester | 248282-11-3

• 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-trifluoromethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-5-trifluoromethyl-3-quinolinecarboxylate；1,2-dihydro-4-hydroxy-5-trifluoromethyl-1-methyl-2-oxoquinoline-3-carboxylic acid ethyl ester；1.2Dihydro-4-hydroxy-5-trifluoromethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester；Ethyl 4-hydroxy-1-methyl-2-oxo-5-(trifluoromethyl)quinoline-3-carboxylate
• CAS: 248282-11-3
• 化学式: C₁₄H₁₂F₃NO₄
• 分子量: 315.249
• InChiKey: IYWKGSRCHFLRJY-UHFFFAOYSA-N

物化性质

• 沸点：
  395.0±42.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-乙基苯胺 、 1,2-Dihydro-4-hydroxy-5-trifluoromethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester 以 甲苯 为溶剂， 反应 6.0h， 以69%的产率得到N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-trifluoromethyl-1-methyl-2-oxo-quinoline-3-carboxamide
  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：

  2-氟-6-(三氟甲基)苯腈 在 4-氨基吡啶 、 盐酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 29.0h， 生成 1,2-Dihydro-4-hydroxy-5-trifluoromethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester
  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

• Quinoline derivatives
  申请人：Active Biotech AB

  公开号：US20020173519A1

  公开（公告）日：2002-11-21

  Compounds of formula (I) 1 and tautomers thereof are effective for the treatment of mammals suffering from diseases resulting from autoimmunity and pathological inflammation.

  化合物式(I)1及其互变异构体对于治疗患有自身免疫和病理性炎症引起的疾病的哺乳动物是有效的。
• QUINOLINE DERIVATIVES
  申请人：Active Biotech AB

  公开号：EP1095021B1

  公开（公告）日：2003-09-17
• US6077851A
  申请人：——

  公开号：US6077851A

  公开（公告）日：2000-06-20
• US6133285A
  申请人：——

  公开号：US6133285A

  公开（公告）日：2000-10-17
• US6593343B2
  申请人：——

  公开号：US6593343B2

  公开（公告）日：2003-07-15