6-Cyclopropyl-4,5-difluoro-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrrolo[3,4-f]quinoline-1,8-dicarboxylic acid 1-ethyl ester | 186749-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Cyclopropyl-4,5-difluoro-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrrolo[3,4-f]quinoline-1,8-dicarboxylic acid 1-ethyl ester
• 英文别名: 6-Cyclopropyl-1-ethoxycarbonyl-4,5-difluoro-3,9-dioxo-1,2-dihydropyrrolo[3,4-f]quinoline-8-carboxylic acid
• CAS: 186749-32-6
• 化学式: C₁₈H₁₄F₂N₂O₆
• 分子量: 392.316
• InChiKey: DEOZXMWGRIILRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 6-Cyclopropyl-4,5-difluoro-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrrolo[3,4-f]quinoline-1,8-dicarboxylic acid 1-ethyl ester 以 吡啶 为溶剂， 反应 1.0h， 以46%的产率得到6-Cyclopropyl-5-fluoro-4-(4-methyl-piperazin-1-yl)-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrrolo[3,4-f]quinoline-1,8-dicarboxylic acid 1-ethyl ester
  参考文献：
  名称：

  Pyrroloquinolones and pyrazoloquinolones as potential antibacterial agents. Synthesis and antibacterial activity

  摘要：

  Diethyl 1-cyclopropyl-5,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3,6-dicarboxylate as a key-intermediate was synthesized via the Dieckmann reaction. The reaction of 4 with nucleophiles proceeded regioselectively at C-5. Facile cyclization between the C-5 and C-6 side chains of the resulting products gave novel pyrroloquinolones 10 and 12 and pyrazoloquinolones 15. They were converted into a series of cyclic amino-substituted pyrroloquinolones 17-21 and pyrazoloquinolones 22-24, and their in vitro antibacterial activities were tested. 1H-Pyrrolo[2,3-f]quinolone 17a and 2H-pyrrolo[3,4-f]quinolone 21a exhibited a potent in vitro antibacterial activity.

  DOI：

  10.1016/s0223-5234(97)86177-6
• 作为产物：
  描述：

  Diethyl 1-cyclopropyl-5,7,8-trifluoro-4-oxoquinoline-3,6-dicarboxylate 在 sodium hydride 作用下， 以 硫酸 、 溶剂黄146 、 甲苯 为溶剂， 反应 20.0h， 生成 6-Cyclopropyl-4,5-difluoro-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrrolo[3,4-f]quinoline-1,8-dicarboxylic acid 1-ethyl ester
  参考文献：
  名称：

  Pyrroloquinolones and pyrazoloquinolones as potential antibacterial agents. Synthesis and antibacterial activity

  摘要：

  Diethyl 1-cyclopropyl-5,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3,6-dicarboxylate as a key-intermediate was synthesized via the Dieckmann reaction. The reaction of 4 with nucleophiles proceeded regioselectively at C-5. Facile cyclization between the C-5 and C-6 side chains of the resulting products gave novel pyrroloquinolones 10 and 12 and pyrazoloquinolones 15. They were converted into a series of cyclic amino-substituted pyrroloquinolones 17-21 and pyrazoloquinolones 22-24, and their in vitro antibacterial activities were tested. 1H-Pyrrolo[2,3-f]quinolone 17a and 2H-pyrrolo[3,4-f]quinolone 21a exhibited a potent in vitro antibacterial activity.

  DOI：

  10.1016/s0223-5234(97)86177-6

文献信息

• Pyrroloquinolones and pyrazoloquinolones as potential antibacterial agents. Synthesis and antibacterial activity
  作者：M Fujita、H Egawa、T Miyamoto、J Nakano、J Matsumoto

  DOI：10.1016/s0223-5234(97)86177-6

  日期：1996.1

  Diethyl 1-cyclopropyl-5,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3,6-dicarboxylate as a key-intermediate was synthesized via the Dieckmann reaction. The reaction of 4 with nucleophiles proceeded regioselectively at C-5. Facile cyclization between the C-5 and C-6 side chains of the resulting products gave novel pyrroloquinolones 10 and 12 and pyrazoloquinolones 15. They were converted into a series of cyclic amino-substituted pyrroloquinolones 17-21 and pyrazoloquinolones 22-24, and their in vitro antibacterial activities were tested. 1H-Pyrrolo[2,3-f]quinolone 17a and 2H-pyrrolo[3,4-f]quinolone 21a exhibited a potent in vitro antibacterial activity.