4-chloro-3-(2-chloro-ethyl)-8-methoxy-quinolin-2-ol | 104295-92-3

• 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: 4-chloro-3-(2-chloro-ethyl)-8-methoxy-quinolin-2-ol
• 英文别名: 4-Chlor-3-(2-chlor-aethyl)-8-methoxy-chinolin-2-ol；4-Chloro-3-(2-chloroethyl)-8-methoxyquinolin-2(1H)-one；4-chloro-3-(2-chloroethyl)-8-methoxy-1H-quinolin-2-one
• CAS: 104295-92-3
• 化学式: C₁₂H₁₁Cl₂NO₂
• 分子量: 272.131
• InChiKey: ORLCEMXECSABAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-3-(2-chloro-ethyl)-8-methoxy-quinolin-2-ol 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 22.0h， 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 7.0h， 生成 4-chloro-3-(2-chloro-ethyl)-8-methoxy-quinolin-2-ol
  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

• 417. The synthesis of dictamnine and γ-fagarine
  作者：M. F. Grundon、N. J. McCorkindale

  DOI：10.1039/jr9570002177

  日期：——
• Ohta; Mori, Proceedings of the Japan Academy, 1957, vol. 33, p. 346,348
  作者：Ohta、Mori

  DOI：——

  日期：——
• 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.