5-amino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 123016-41-1

• 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: 5-amino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 5-amino-1-cyclopropyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 123016-41-1
• 化学式: C₁₈H₂₁FN₄O₃
• 分子量: 360.388
• InChiKey: GTFYODRYQGFYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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-amino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  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。
• 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
• US5013841A
  申请人：——

  公开号：US5013841A

  公开（公告）日：1991-05-07