1-环丙基-8-乙氧基-6-氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸 | 182868-72-0

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 喹诺酮类药
• 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: 1-环丙基-8-乙氧基-6-氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸
• 中文别名: 8-乙氧基加替沙星
• 英文名称: 1-Cyclopropyl-8-ethoxy-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-8-ethoxy-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 182868-72-0
• 化学式: C₂₀H₂₄FN₃O₄
• 分子量: 389.427
• InChiKey: OWEQWFYVHJAGCR-UHFFFAOYSA-N

物化性质

• 沸点：
  613.4±55.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为产物：
  描述：

  1-环丙基-6,7-二氟-1,4-二氢-8-乙氧基-4-氧代-3-喹啉羧酸 、 2-甲基哌嗪 反应 2.0h， 以50%的产率得到1-环丙基-8-乙氧基-6-氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸
  参考文献：
  名称：

  Synthesis of norfloxacin analogues catalyzed by Lewis and Brönsted acids: An alternative pathway

  摘要：

  An alternative synthetic pathway to prepare norfloxacin analogues is presented. Three Lewis acids (CeCl3 center dot 7H(2)O, AlCl3 center dot 6H(2)O, ZnCl2) and one Bronsted acid (TsOH) were tested as catalysts in the preparation of 3,4-difluoroacrylate. Cyclization of this acrylate at 55 degrees C was achieved with the use of Eaton's reagent (P2O5/MeSO3H) a known Bronsted acid. The fluoroquinolone-boron complex presented high yields on C-7 nucleophilic substitution of the fluorine atom by different heterocyclic amines with low, medium and strong nucleophilic character. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.07.002

文献信息

• The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents
  作者：Joseph P. Sanchez、Rocco D. Gogliotti、John M. Domagala、Stephen J. Gracheck、Michael D. Huband、Josephine A. Sesnie、Michael A. Cohen、Martin A. Shapiro

  DOI：10.1021/jm00022a013

  日期：1995.10

  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.