加替环合酯C | 172602-83-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 加替环合酯C
• 中文别名: 1-环丙基-8-乙氧基-6,7-二氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯；加替沙星杂质H；1-环丙基-6,7-二氟-8-乙氧基-4-氧代-1,4-二氢-3-喹啉羧酸乙酯；莫西沙星杂质U；莫西沙星EP杂质10；莫西沙星杂质10；乙基1-环丙基-8-乙氧基-6,7-二氟-4-氧代-1,4-二氢喹啉-3-甲酸酯；乙基 1-环丙基-8-乙氧基-6,7-二氟-4-氧代-1,4-二氢喹啉-3-甲酸酯
• 英文名称: ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
• 英文别名: Ethyl 1-cyclopropyl-8-ethoxy-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate；ethyl 1-cyclopropyl-8-ethoxy-6,7-difluoro-4-oxoquinoline-3-carboxylate
• CAS: 172602-83-4
• 化学式: C₁₇H₁₇F₂NO₄
• 分子量: 337.323
• InChiKey: HVSSSDATQQUFJP-UHFFFAOYSA-N

物化性质

• 熔点：
  147-150°C
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 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：
  55.8
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  加替环合酯C 在 镍 sodium hydroxide 、 硫酸 、 氢气 、 potassium nitrate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 30.0 ℃ 、206.84 kPa 条件下， 反应 59.0h， 生成 5-Amino-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxoquinoline-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：

  莫西沙星杂质35 在 2,2'-联吡啶 、 正丁基锂 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 43.0h， 生成 加替环合酯C
  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