1-(2-methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline | 140633-33-6

• 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-methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline
• 英文别名: 6-methoxy-1-(2-methylphenyl)-3,5-dihydro-2H-pyrrolo[3,2-c]quinolin-4-one
• CAS: 140633-33-6
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: WCTQMKSQQXEMSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1-(2-methylphenyl)-4-(methylamino)-6-methoxy-2,3-dihydropyrrolo<3,2-c>quinoline
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 2. 1-Arylpyrrolo[3,2-c]quinolines: effect of the 4-substituent

  摘要：

  Further work on compounds 1 has identified the 4-position as a site where substantial modifications are tolerated, leading to analogues which are more potent and less toxic than those described previously. The best compound in the series is 13a (SK&F 96356), which is a potent inhibitor of gastric acid secretion in both the pentagastrin-stimulated rat and the histamine-stimulated dog. This compound shows reversible, K+-competitive binding to the enzyme. Because of its fluorescent properties, it is also proving useful in vitro as a probe of the structure and function of the (H+/K+)-ATPase.

  DOI：

  10.1021/jm00088a021
• 作为产物：
  描述：

  6-methoxy-3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 在 盐酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 生成 1-(2-methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 2. 1-Arylpyrrolo[3,2-c]quinolines: effect of the 4-substituent

  摘要：

  Further work on compounds 1 has identified the 4-position as a site where substantial modifications are tolerated, leading to analogues which are more potent and less toxic than those described previously. The best compound in the series is 13a (SK&F 96356), which is a potent inhibitor of gastric acid secretion in both the pentagastrin-stimulated rat and the histamine-stimulated dog. This compound shows reversible, K+-competitive binding to the enzyme. Because of its fluorescent properties, it is also proving useful in vitro as a probe of the structure and function of the (H+/K+)-ATPase.

  DOI：

  10.1021/jm00088a021

文献信息

• Process for preparing 1-aryl-4-oxopyrrolo \x9b3,2-c! quinoline derivatives
  申请人：Korea Research Institute of Chemical Technology

  公开号：US05914402A1

  公开（公告）日：1999-06-22

  The present invention relates to a process for preparing 1-aryl-4-oxopyrrolo\x9b3,2-c!quinoline derivatives through reaction of 4-oxofuro\x9b3,2-c! quinoline compounds with aniline compounds under mild conditions in a single step, wherein 1-aryl-4-oxopyrrolo\x9b3,2-c!quinoline derivatives having various substituents may be prepared in high yield, so that the 1-aryl-4-oxopyrrolo\x9b3,2-c!quinoline derivatives may be utilized as an intermediate for producing a reversible inhibitor of gastric acid secretion.

  本发明涉及一种制备1-芳基-4-氧代吡咯并[3,2-c]喹啉衍生物的方法，通过在温和条件下一步反应4-氧代呋喃并[3,2-c]喹啉化合物与苯胺化合物，可以制备出具有不同取代基的高产率的1-芳基-4-氧代吡咯并[3,2-c]喹啉衍生物，因此，这些化合物可以用作产生可逆胃酸分泌抑制剂的中间体。
• Kim, Sung Soo; Cheon, Hyac Gyeong; Kang, Seung Kyu, Heterocycles, 1998, vol. 48, # 2, p. 221 - 226
  作者：Kim, Sung Soo、Cheon, Hyac Gyeong、Kang, Seung Kyu、Yum, Eul Kgun、Choi, Joong-Kwon

  DOI：——

  日期：——
• US5914402A
  申请人：——

  公开号：US5914402A

  公开（公告）日：1999-06-22
• Reversible inhibitors of the gastric (H+/K+)-ATPase. 2. 1-Arylpyrrolo[3,2-c]quinolines: effect of the 4-substituent
  作者：Colin A. Leach、Thomas H. Brown、Robert J. Ife、David J. Keeling、Shiona M. Laing、Michael E. Parsons、Carolyn A. Price、Kenneth J. Wiggall

  DOI：10.1021/jm00088a021

  日期：1992.5

  Further work on compounds 1 has identified the 4-position as a site where substantial modifications are tolerated, leading to analogues which are more potent and less toxic than those described previously. The best compound in the series is 13a (SK&F 96356), which is a potent inhibitor of gastric acid secretion in both the pentagastrin-stimulated rat and the histamine-stimulated dog. This compound shows reversible, K+-competitive binding to the enzyme. Because of its fluorescent properties, it is also proving useful in vitro as a probe of the structure and function of the (H+/K+)-ATPase.