5,7-Dichloro-4-[1-(4-methanesulfonylamino-phenylcarbamoyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid ethyl ester | 635319-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,7-Dichloro-4-[1-(4-methanesulfonylamino-phenylcarbamoyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid ethyl ester
• CAS: 635319-84-5
• 化学式: C₂₁H₂₁Cl₂N₃O₅S
• 分子量: 498.387
• InChiKey: OGVWAGLDJQJBOT-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113.6
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,7-Dichloro-4-[1-(4-methanesulfonylamino-phenylcarbamoyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 以90%的产率得到Sodium; 5,7-dichloro-4-[1-(4-methanesulfonylamino-phenylcarbamoyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-quinoline-2-carboxylate
  参考文献：
  名称：

  Enantiomerically pure tetrahydroquinoline derivatives as in vivo potent antagonists of the glycine binding site associated to the NMDA receptor

  摘要：

  To identify neuroprotective agents after stroke, new substituted tetrahydroquinoline derivatives were designed as antagonists of the glycine binding site associated to the NMDA receptor, satisfying the key pharmacophoric requirements. In particular, the racemate 3c exhibited outstanding in vivo activity in the MCAo model in rats, when given iv both pre- and post-ischemia. Pure enantiomers 3c-(+) and 3c-(-) have been prepared following an original synthetic route. Despite the significant difference of activity observed in vitro, they shown similar neuroprotective profile in the MCAo model in rats. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.06.001
• 作为产物：
  描述：

  在 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 5,7-Dichloro-4-[1-(4-methanesulfonylamino-phenylcarbamoyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically pure tetrahydroquinoline derivatives as in vivo potent antagonists of the glycine binding site associated to the NMDA receptor

  摘要：

  To identify neuroprotective agents after stroke, new substituted tetrahydroquinoline derivatives were designed as antagonists of the glycine binding site associated to the NMDA receptor, satisfying the key pharmacophoric requirements. In particular, the racemate 3c exhibited outstanding in vivo activity in the MCAo model in rats, when given iv both pre- and post-ischemia. Pure enantiomers 3c-(+) and 3c-(-) have been prepared following an original synthetic route. Despite the significant difference of activity observed in vitro, they shown similar neuroprotective profile in the MCAo model in rats. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.06.001