1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline | 122456-57-9

• 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: 1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline
• 英文别名: 1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinolin；6-methyl-1-(2-methylphenyl)-3,5-dihydro-2H-pyrrolo[3,2-c]quinolin-4-one
• CAS: 122456-57-9
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: PXLQUAOLDGDVNL-UHFFFAOYSA-N

物化性质

• 沸点：
  498.2±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline 在 钯 silica gel 作用下， 以 二苯醚 为溶剂， 反应 4.0h， 以to obtain 245 mg of desired compound as solid in 85%的产率得到1-(2-methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo<3,2-c>quinoline
  参考文献：
  名称：

  Process for preparing 1-aryl-4-oxopyrrolo \x9b3,2-c! quinoline derivatives

  摘要：

  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。

  公开号：

  US05914402A1
• 作为产物：
  描述：

  2-(2-ethoxyethyl)-N,N'-bis(2-methylphenyl)malonodiamide 以 二苯醚 、 Petroleum ether 为溶剂， 生成 1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Dihydropyrrolo quinoline derivatives

  摘要：

  1,4-取代的2,3-二氢吡咯并[3,2-c]喹啉是H.sup.+ K.sup.+ ATP酶活性的抑制剂，也可作为胃酸分泌抑制剂使用。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。

  公开号：

  US05051508A1

文献信息

• Quinoline derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：SMITHKLINE BEECHAM INTERCREDIT B.V.

  公开号：EP0307078A1

  公开（公告）日：1989-03-15

  in which R¹ to R⁴ are the same or different and are inter alia, each hydrogen, C₁₋₄alkyl, C₁₋₆alkoxy, phenyl, C₁₋₆alkylthio, C₁₋₄alkanoyl, amino, R⁵ to R⁹ are the same or different and are each hydrogen, C₁₋₆alkyl, C₁₋₆alkoxy, C₁₋₆alkylthio, halogen, cyano, amino, hydroxy, carbamoyl, carboxy, C₁₋₆alkanoyl, trifluoromethyl or nitro, R¹⁰ is inter alia hydrogen, C₁₋₆alkyl, C₁₋₆alkoxy, halogen, hydroxy, -CH₂OH, C₁₋₆alkylthio, NH(CH₂)nOH in which n is 0 to 4 or amino; and A is -(CH₂)₂-, (CH₂)₃- ­or -CH=CH-; processes for their preparation, pharmaceutical compositions containing them and their use in therapy as inhibitors of gastric acid secretion.

  C₁₋₄烷硫基、C₁₋₄烷酰基、氨基、R⁵至 R⁹相同或不同且各自为氢、C₁₋₆alkyl、C₁₋₆alkoxy、C₁₋₆烷硫基、卤素、氰基、氨基、羟基、氨基甲酰基、羧基、C₁₋₆烷酰基、三氟甲基或硝基，R¹⁰除其他外为氢、C₁₋₆烷基、C₁₋₆烷氧基、卤素、羟基、-CH₂OH、C₁₋₆烷硫基、NH(CH₂)nOH（其中 n 为 0 至 4）或氨基；和 A 是-(CH₂)₂-、(CH₂)₃- 或-CH=CH-；它们的制备工艺、含有它们的药物组合物以及它们作为胃酸分泌抑制剂在治疗中的用途。
• 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.
• 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：——
• US5051508A
  申请人：——

  公开号：US5051508A

  公开（公告）日：1991-09-24
• 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-氧基吡咯并[3,2-c]喹啉衍生物的方法，通过在温和条件下一步反应4-氧基呋喃并[3,2-c]喹啉化合物与苯胺化合物，可高产率制备具有各种取代基的1-芳基-4-氧基吡咯并[3,2-c]喹啉衍生物，使得这些衍生物可以作为产生胃酸分泌可逆抑制剂的中间体。