ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate | 172602-85-6

• 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: ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
• 英文别名: Ethyl 5-amino-1-cyclopropyl-8-ethoxy-6,7-difluoro-4-oxoquinoline-3-carboxylate
• CAS: 172602-85-6
• 化学式: C₁₇H₁₈F₂N₂O₄
• 分子量: 352.338
• InChiKey: RDJFYLDGJSVESV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate 在 sodium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 37.0h， 生成 5-Amino-7-(3-amino-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

  摘要：

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.

  DOI：

  10.1021/jm00022a013
• 作为产物：
  描述：

  2,4,5-三氟-3-羟基苯甲酸 在 镍 2,2'-联吡啶 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 硫酸 、 氢气 、 乙酸酐 、 sodium hydride 、 potassium nitrate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -30.0~30.0 ℃ 、206.84 kPa 条件下， 反应 104.0h， 生成 ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
  参考文献：
  名称：

  The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

  摘要：

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.

  DOI：

  10.1021/jm00022a013