ethyl 1,2-dihydro-4-hydroxy-1-methyl-5,6-methylenedioxy-2-oxo-3-quinolinecarboxylate | 248282-15-7

• 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 1,2-dihydro-4-hydroxy-1-methyl-5,6-methylenedioxy-2-oxo-3-quinolinecarboxylate
• 英文别名: 1,2-dihydro 4-hydroxy-1-methyl-2-oxo-5,6-methylenedioxy-quinoline-3-carboxylic acid ethyl ester；1,2-dihydro-4-hydroxy-1-methyl-2-oxo-5,6-methylenedioxy-quinoline-3-carboxylic acid ethyl ester；1,2-dihydro-4-hydroxy-1-methyl-2-oxo-5,6-methylenedioxyquinoline-3-carboxylic acid ethyl ester；ethyl 9-hydroxy-6-methyl-7-oxo-[1,3]dioxolo[4,5-f]quinoline-8-carboxylate
• CAS: 248282-15-7
• 化学式: C₁₄H₁₃NO₆
• 分子量: 291.26
• InChiKey: STCYOJXCIYBAAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1,2-dihydro-4-hydroxy-1-methyl-5,6-methylenedioxy-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 N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5,6-methylenedioxy-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：

  N-Boc-5,6-methylenedioxyanthranilic acid 在 盐酸 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl 1,2-dihydro-4-hydroxy-1-methyl-5,6-methylenedioxy-2-oxo-3-quinolinecarboxylate
  参考文献：
  名称：

  QUINOLINE DERIVATIVES

  摘要：

  公开号：

  EP1095021B1

文献信息

• [EN] QUINOLINE DERIVATIVES<br/>[FR] DERIVES DE QUINOLINE
  申请人：ACTIVE BIOTECH AB

  公开号：WO2000003991A1

  公开（公告）日：2000-01-27

  The invention is related to compounds of general formula (I), wherein R is methyl, ethyl, n-propyl, iso-propyl, n-butyl or allyl; R' is methyl, methoxy, fluoro, chloro, bromo, trifluoromethyl, or OCHxFy, wherein x = O - 2, y = 1 - 3 with the proviso that x + y = 3; R'' is hydrogen, fluoro or chloro; with the proviso that R'' is fluoro or chloro only when R' is fluoro; R4 is hydrogen or pharmaceutically acceptable inorganic or organic cations; R5 is ethyl, n-propyl, iso-propyl, methoxy, ethoxy, chloro, bromo, trifluoromethyl, OCHxFy, or OCH2CHxFy wherein x = 0 - 2, y = 1 - 3 with the proviso that x + y = 3; R6 is hydrogen; or R5, and R6 taken together are methylenedioxy; and any tautomer thereof. The invention also relates to pharmaceutical compositions containing a compound of general formula (I) together with a pharmaceutically acceptable carrier. Included are also processes for the preparation of the compounds of formula (I), as well as methods for the treatment of mammals suffering from diseases resulting from autoimmunity and pathological inflammation by administering of a compound having formula (I) to said mammal.

  该发明涉及通式（I）的化合物，其中R为甲基，乙基，正丙基，异丙基，正丁基或烯丙基；R'为甲基，甲氧基，氟代，氯代，溴代，三氟甲基或OCHxFy，其中x = O-2，y = 1-3，但需满足x + y = 3；R''为氢，氟代或氯代；但需满足当R'为氟代时，R''仅为氟代或氯代；R4为氢或药学上可接受的无机或有机阳离子；R5为乙基，正丙基，异丙基，甲氧基，乙氧基，氯代，溴代，三氟甲基，OCHxFy或OCH2CHxFy，其中x = 0-2，y = 1-3，但需满足x + y = 3；R6为氢；或R5和R6一起为亚甲二氧基；以及其任何互变异构体。该发明还涉及含有通式（I）的化合物和药学上可接受的载体的制药组合物。还包括制备通式（I）化合物的方法，以及通过向哺乳动物施用具有通式（I）的化合物来治疗由自身免疫和病理性炎症引起的疾病的方法。
• 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。
• 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