6-Cyclopropyl-4,5-difluoro-1-methyl-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrazolo[3,4-f]quinoline-8-carboxylic acid ethyl ester | 186749-35-9

• 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-Cyclopropyl-4,5-difluoro-1-methyl-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrazolo[3,4-f]quinoline-8-carboxylic acid ethyl ester
• 英文别名: ethyl 6-cyclopropyl-4,5-difluoro-1-methyl-3,9-dioxo-2H-pyrazolo[3,4-f]quinoline-8-carboxylate
• CAS: 186749-35-9
• 化学式: C₁₇H₁₅F₂N₃O₄
• 分子量: 363.321
• InChiKey: RWDPKCDLDAPJHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-Cyclopropyl-4,5-difluoro-1-methyl-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrazolo[3,4-f]quinoline-8-carboxylic acid ethyl ester 以 硫酸 、 溶剂黄146 、 乙腈 为溶剂， 反应 2.17h， 生成 6-Cyclopropyl-5-fluoro-1-methyl-4-(4-methyl-piperazin-1-yl)-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrazolo[3,4-f]quinoline-8-carboxylic acid
  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 2,4,5,6-tetrafluoroisophthalate 在 potassium tert-butylate 、 溴 、 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 6.5h， 生成 6-Cyclopropyl-4,5-difluoro-1-methyl-3,9-dioxo-2,3,6,9-tetrahydro-1H-pyrazolo[3,4-f]quinoline-8-carboxylic acid 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