5-氨基-1-环丙基-6-氟-4-氧代-7-哌嗪-1-基喹啉-3-羧酸 | 123016-42-2

• 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: 5-氨基-1-环丙基-6-氟-4-氧代-7-哌嗪-1-基喹啉-3-羧酸
• 英文名称: 5-amino-1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazinylquinoline-3-carboxylic acid；3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-；5-amino-1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 123016-42-2
• 化学式: C₁₇H₁₉FN₄O₃
• 分子量: 346.361
• InChiKey: YDCDVKGBYXKGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  98.9
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 在 盐酸 作用下， 以 吡啶 、 水 为溶剂， 反应 24.0h， 生成 5-氨基-1-环丙基-6-氟-4-氧代-7-哌嗪-1-基喹啉-3-羧酸
  参考文献：
  名称：

  Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship

  摘要：

  A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and Ni (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.

  DOI：

  10.1021/jm00107a039

文献信息

• Oxo quinoline derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US05013841A1

  公开（公告）日：1991-05-07

  A quinoline derivative of the formula ##STR1## wherein Z is an amino group or a halogen atom, and R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, and an ester thereof and a salt of the derivative or the ester and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful as antibacterial agents.

  一种喹啉衍生物的化学式为##STR1##，其中Z是氨基团或卤素原子，R.sub.1、R.sub.2和R.sub.3相同或不同，每个代表氢原子或具有1至5个碳原子的较低烷基基团，以及其酯和衍生物的盐和其制备方法。这些化合物表现出优异的抗菌活性，并可用作抗菌剂。
• Quinoline derivatives and antibacterial agent containing them
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US05164392A1

  公开（公告）日：1992-11-17

  A quinoline derivative of the formula ##STR1## wherein Z is an amino group or a halogen atom, and R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, and an ester thereof and a salt of the derivative or the ester and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful as antibacterial agents.

  一种喹啉衍生物的公式为##STR1##其中Z是氨基或卤素原子，R.sub.1，R.sub.2和R.sub.3相同或不同，每个表示氢原子或具有1至5个碳原子的较低烷基基团，以及其酯和衍生物或酯的盐以及其制备方法。这些化合物显示出优异的抗菌活性，并可用作抗菌剂。
• 5-Amino-8-methyl-7-pyrrolidinylquinoline-3-carboxylic acid derivative
  申请人：HOKURIKU SEIYAKU CO., LTD.

  公开号：EP0641793A1

  公开（公告）日：1995-03-08

  A 5-amino-8-methyl-7-pyrrolidinylquinoline-3-carboxylic acid derivative represented by the general formula: wherein R¹ is a hydrogen atom or a lower alkyl group; R² is a hydrogen atom, a lower alkyl group, a lower alkanoyl group, a halogenated lower alkanoyl group or a residue of carboxylic acid ester; R³ is a hydrogen atom or a lower alkyl group; R⁴ , R⁵ or R⁶ are each independently a hydrogen atom or a lower alkyl group; or two of R⁴, R⁵ and R⁶ may be taken together to form a -(CH₂) n - group wherein n is 1 or 2, a stereoisomer thereof, or a pharmacologically acceptable salt thereof, the process for preparing these compounds, a pharmaceutical composition comprising an effective amount of these compounds and methods for the treatment of infectious diseases through the administration to patients of an effective amount of these compounds, and intermediates of these compounds are disclosed. These compounds are effective as antibacterial agents.

  由通式代表的 5-氨基-8-甲基-7-吡咯烷基喹啉-3-羧酸衍生物： 其中 R¹ 是氢原子或低级烷基；R² 是氢原子、低级烷基、低级烷酰基、卤代低级烷酰基或羧酸酯残基；R³是氢原子或低级烷基； R⁴、R⁵或 R⁶各自独立地是氢原子或低级烷基；或 R⁴、R⁵和 R⁶中的两个可结合在一起形成-(CH₂) n-基团，其中 n 是 1 或 2、 公开了这些化合物的立体异构体或其药理学上可接受的盐、制备这些化合物的工艺、包含有效量这些化合物的药物组合物和通过向患者施用有效量这些化合物来治疗传染性疾病的方法，以及这些化合物的中间体。 这些化合物是有效的抗菌剂。
• DOMAGALA, JOHN M.;BRIDGES, ALEX J.;CULBERTSON, TOWNLEY P.;GAMBINO, LAURA;+, J. MED. CHEM., 34,(1991) N, C. 1142-1154
  作者：DOMAGALA, JOHN M.、BRIDGES, ALEX J.、CULBERTSON, TOWNLEY P.、GAMBINO, LAURA、+

  DOI：——

  日期：——
• Novel quinoline derivatives, processes for preparation thereof and antibacterial agent containing them
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0312085B1

  公开（公告）日：1993-05-12