3-[1-(2-Methoxy-phenylamino)-meth-(E)-ylidene]-tetrahydro-pyran-2-one | 122456-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[1-(2-Methoxy-phenylamino)-meth-(E)-ylidene]-tetrahydro-pyran-2-one
• 英文别名: 3-(2-Methoxyphenylaminomethylene)tetrahydropyran-2-one；3-[(2-methoxyanilino)methylidene]oxan-2-one
• CAS: 122456-54-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: RRBFGVWNRIZVRB-UHFFFAOYSA-N

物化性质

• 沸点：
  416.9±45.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  3-[1-(2-Methoxy-phenylamino)-meth-(E)-ylidene]-tetrahydro-pyran-2-one 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 97.0h， 生成 7-methoxy-1-(2-methylphenyl)-1,2,3,4-tetrahydropyridino<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
• 作为产物：
  描述：

  邻茴香胺盐酸盐 、 sodium salt of 3-(hydroxymethylene)tetrahydropyran-2-one 以 乙醇 为溶剂， 反应 2.0h， 以55%的产率得到3-[1-(2-Methoxy-phenylamino)-meth-(E)-ylidene]-tetrahydro-pyran-2-one
  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

• Dihydropyrrolo quinoline derivatives
  申请人：SmithKline Beckman Intercredit B.V.

  公开号：US05051508A1

  公开（公告）日：1991-09-24

  1,4-Substituted 2,3-dihydropyrrolo[3,2-c]quinolines which are inhibitors of H.sup.+ K.sup.+ ATPase activity and useful as inhibitors of gastric acid secretion. A compound of the invention is 1-(2-methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline.

  1,4-取代的2,3-二氢吡咯并[3,2-c]喹啉是H.sup.+ K.sup.+ ATPase活性的抑制剂，可用作胃酸分泌的抑制剂。该发明的化合物是1-(2-甲基苯基)-4-氨基-6-甲基-2,3-二氢吡咯并[3,2-c]喹啉。