ethyl 1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-3-quinolinecarboxylate | 675574-93-3

• 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: ethyl 1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-3-quinolinecarboxylate
• 英文别名: 4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester；3-Quinolinecarboxylic acid,1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-,ethyl ester；ethyl 4-hydroxy-1,6-dimethyl-2-oxoquinoline-3-carboxylate
• CAS: 675574-93-3
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: CCNPWNUEXNSJFA-UHFFFAOYSA-N

物化性质

• 沸点：
  401.8±45.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 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：
  4

反应信息

• 作为反应物：
  描述：

  N-乙基苯胺 、 ethyl 1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-3-quinolinecarboxylate 以 甲苯 为溶剂， 反应 6.0h， 以69%的产率得到3-Quinolinecarboxamide,n-ethyl-1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-n-phenyl-
  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：

  丙二酸二乙酯 、 N,5-二甲基靛红酸酐 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以87%的产率得到ethyl 1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-3-quinolinecarboxylate
  参考文献：
  名称：

  [EN] INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR AND METHODS FOR IDENTIFYING THE SAME
  [FR] INHIBITEURS DU FACTEUR D'INHIBITION DE LA MIGRATION DES MACROPHAGES(MIF) ET PROCEDES D'IDENTIFICATION DE CEUX-CI

  摘要：

  公开号：

  WO2004074218A3

文献信息

• Inhibitors of macrophage migration inhibitory factor and methods for identifying the same
  申请人：——

  公开号：US20040204586A1

  公开（公告）日：2004-10-14

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: 1 including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF的抑制剂，可用于治疗多种疾病，包括与MIF活性相关的病理条件的治疗。MIF的抑制剂具有以下结构：包括立体异构体，前药和其药学上可接受的盐，其中n，R1，R2，R3，R4，X和Z的定义如本文所述。还提供了含有MIF抑制剂与药学上可接受的载体组合的组合物，以及使用它们的方法。
• INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR AND METHODS FOR IDENTIFYING THE SAME
  申请人：Sircar Jagadish

  公开号：US20070238736A9

  公开（公告）日：2007-10-11

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了抑制MIF的抑制剂，其在治疗多种疾病方面具有用途，包括治疗与MIF活性相关的病理条件。 MIF的抑制剂具有以下结构：包括立体异构体，前药和其药学上可接受的盐，其中n，R1，R2，R3，R4，X和Z的定义如本文所述。还提供了含有MIF抑制剂和药学上可接受的载体组合的组合物，以及使用它们的方法。
• EP1594501A4
  申请人：——

  公开号：EP1594501A4

  公开（公告）日：2007-01-24
• US7173036B2
  申请人：——

  公开号：US7173036B2

  公开（公告）日：2007-02-06
• US7235546B2
  申请人：——

  公开号：US7235546B2

  公开（公告）日：2007-06-26