5-(Acetyl-benzyl-amino)-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester | 123016-66-0

• 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-(Acetyl-benzyl-amino)-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(N-acetylbenzylamino)-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate；ethyl 5-[acetyl(benzyl)amino]-1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylate
• CAS: 123016-66-0
• 化学式: C₂₄H₂₂F₂N₂O₄
• 分子量: 440.446
• InChiKey: SIXXBMOWQJMYIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(Acetyl-benzyl-amino)-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 RaNi 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
  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
• 作为产物：
  描述：

  3,4,6-三氟-2-[(苯基甲基)氨基]苯甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 potassium tert-butylate 、 乙酸酐 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 28.5h， 生成 5-(Acetyl-benzyl-amino)-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  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

• 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。
• 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，其化学式为##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，分别代表氢原子或具有1至5个碳原子的较低烷基基团，以及其酯和衍生物或酯和衍生物的盐的制备方法。这些化合物表现出出色的抗菌活性，并可用作抗菌剂。
• 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
• US5164392A
  申请人：——

  公开号：US5164392A

  公开（公告）日：1992-11-17