Methyl 8-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-acetate | 149264-77-7

• 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: Methyl 8-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-acetate
• 英文别名: Methyl 2-[8-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate
• CAS: 149264-77-7
• 化学式: C₁₉H₂₀ClNO₃
• 分子量: 345.826
• InChiKey: ZRWFZKCFZRZYHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 8-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-acetate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 8-Chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-acetic acid
  参考文献：
  名称：

  Synthesis and antirheumatic activity of novel tetrahydro-6-quinolineacetic acid derivatives

  摘要：

  A study of the structural optimization of tetrahydroquinoline-6-acetic acid and the development of a novel DMARD with prompt action are detailed. (S)-(+)-8-Chloro-1,2,3,4-tetrahydro-2-trifluoromethyl-6-quinolineacetic acid (IRA-378) exhibits the: effect against both acute and chronic inflammations. It also has suppressive effects of bone destruction in adjuvant arthritis and Ca release from bones in vitro. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00262-x
• 作为产物：
  描述：

  4-氨基-3-氯苯-1-乙酸甲酯 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 三乙胺 、 三氯氧磷 作用下， 以 二苯醚 、 乙醇 、 苯 为溶剂， 生成 Methyl 8-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-acetate
  参考文献：
  名称：

  Synthesis and antirheumatic activity of novel tetrahydro-6-quinolineacetic acid derivatives

  摘要：

  A study of the structural optimization of tetrahydroquinoline-6-acetic acid and the development of a novel DMARD with prompt action are detailed. (S)-(+)-8-Chloro-1,2,3,4-tetrahydro-2-trifluoromethyl-6-quinolineacetic acid (IRA-378) exhibits the: effect against both acute and chronic inflammations. It also has suppressive effects of bone destruction in adjuvant arthritis and Ca release from bones in vitro. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00262-x

文献信息

• NOVEL CYCLIC AMINOPHENYLACETIC ACID DERIVATIVE, PRODUCTION THEREOF, AND IMMUNE RESPONSE MODULATOR CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0538477A1

  公开（公告）日：1993-04-28

  A novel cyclic aminophenylacetic acid derivative which has an immune response modulatory activity, represented by general formula (1), an optical isomer thereof and salts thereof, a process for producing the same, and a remedy for autoimmune diseases containing the same as an active ingredient. In Formula (1), R and R¹ represent each independently hydrogen or C₁ to C₃ lower alkyl; R² represents trifluoromethyl or phenyl which may be substituted by one to three groups selected among halogen, methoxy and combinations thereof; and X represents hydrogen, C₁ to C₃ lower alkyl, C₁ to C₃ lower alkoxy, cyano, thiocyano, trimethylsilylethynyl, phenyl which may be substituted by one to three groups selected among halogen, methoxy, methyl and combinations thereof, carbamoyl, carboxyl, C₁ to C₃ lower alkoxycarbonyl, acetyl, benzoyl, nitro, amino, C₁ to C₃ lower alkanoylamino, benzoylamino which may be substituted, phenylsulfonylamino which may be substituted, C₁ to C₃ lower alkylthio, C₁ to C₃ lower alkylsulfinyl, C₁ to C₃ lower alkylsulfonyl or halogen.

  一种具有免疫反应调节活性的新型环氨基苯乙酸衍生物（通式(1)表示）、其光学异构体及其盐类、生产该衍生物的工艺以及含有该衍生物作为活性成分的治疗自身免疫性疾病的药物。在式 (1) 中，R 和 R¹ 各自独立地代表氢或 C₁ 至 C₃ 低级烷基；R² 代表三氟甲基或苯基，可被一至三个选自卤素、甲氧基及其组合的基团取代；X 代表氢、C₁～C₃低级烷基、C₁～C₃低级烷氧基、氰基、硫代氰基、三甲基硅乙炔基、可被一至三个选自卤素、甲氧基、甲基及其组合的基团取代的苯基、氨基甲酰基、羧基、C₁至 C₃低级烷氧羰基、乙酰基、苯甲酰基、硝基、氨基、C₁至 C₃低级烷酰胺基、可被取代的苯甲酰胺基、C₁至 C₃低级烷硫基、C₁至 C₃低级烷基亚磺酰基、C₁至 C₃低级烷基磺酰基或卤素。
• US5359076A
  申请人：——

  公开号：US5359076A

  公开（公告）日：1994-10-25
• Synthesis and antirheumatic activity of novel tetrahydro-6-quinolineacetic acid derivatives
  作者：Yasushi Kohno、Katsuya Awano、Mitsutomo Miyashita、Takayoshi Ishizaki、Kazuhiko Kuriyama、Yasuhiko Sakoe、Shinji Kudoh、Koji Saito、Eisuke Kojima

  DOI：10.1016/s0960-894x(97)00262-x

  日期：1997.6

  A study of the structural optimization of tetrahydroquinoline-6-acetic acid and the development of a novel DMARD with prompt action are detailed. (S)-(+)-8-Chloro-1,2,3,4-tetrahydro-2-trifluoromethyl-6-quinolineacetic acid (IRA-378) exhibits the: effect against both acute and chronic inflammations. It also has suppressive effects of bone destruction in adjuvant arthritis and Ca release from bones in vitro. (C) 1997 Elsevier Science Ltd.