6-Fluoro-4-methyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline | 122456-65-9

• 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: 6-Fluoro-4-methyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline
• 英文别名: 6-fluoro-4-methyl-1-(2-methylphenyl)-2,3-dihydropyrrolo[3,2-c]quinoline
• CAS: 122456-65-9
• 化学式: C₁₉H₁₇FN₂
• 分子量: 292.356
• InChiKey: WGIOXVXYRNFDJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 22.5h， 生成 6-Fluoro-4-methyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 1. 1-Aryl-4-methylpyrrolo[3,2-c]quinolines as conformationally restrained analogs of 4-(arylamino)quinolines

  摘要：

  The 4-(arylamino)quinoline 4, previously described as an antiulcer compound, is shown to be an inhibitor of the gastric (H+/K+)-ATPase. It is postulated that 1-arylpyrrolo[3,2-c]quinolines 6 act as conformationally restrained analogues of 4. A series of derivatives of 6 has been prepared and shown to be potent inhibitors of the target enzyme in vitro. Substitution in the ortho position of the aryl ring is important for activity. Unsaturation in the 5-membered ring makes little difference, but introduction of heteroatoms into the same ring markedly reduces activity. In more detailed kinetic experiments, 15c and 4 both show reversible, K(+)-competitive binding to the enzyme, with submicromolar Ki values. The compounds appear to act at the lumenal face of the enzyme and to require protonation for activity. Several compounds in the series are shown to be potent inhibitors of pentagastrin-stimulated acid secretion in the rat.

  DOI：

  10.1021/jm00164a010

文献信息

• Reversible inhibitors of the gastric (H+/K+)-ATPase. 1. 1-Aryl-4-methylpyrrolo[3,2-c]quinolines as conformationally restrained analogs of 4-(arylamino)quinolines
  作者：Thomas H. Brown、Robert J. Ife、David J. Keeling、Shiona M. Laing、Colin A. Leach、Michael E. Parsons、Carolyn A. Price、David R. Reavill、Kenneth J. Wiggall

  DOI：10.1021/jm00164a010

  日期：1990.2

  The 4-(arylamino)quinoline 4, previously described as an antiulcer compound, is shown to be an inhibitor of the gastric (H+/K+)-ATPase. It is postulated that 1-arylpyrrolo[3,2-c]quinolines 6 act as conformationally restrained analogues of 4. A series of derivatives of 6 has been prepared and shown to be potent inhibitors of the target enzyme in vitro. Substitution in the ortho position of the aryl ring is important for activity. Unsaturation in the 5-membered ring makes little difference, but introduction of heteroatoms into the same ring markedly reduces activity. In more detailed kinetic experiments, 15c and 4 both show reversible, K(+)-competitive binding to the enzyme, with submicromolar Ki values. The compounds appear to act at the lumenal face of the enzyme and to require protonation for activity. Several compounds in the series are shown to be potent inhibitors of pentagastrin-stimulated acid secretion in the rat.