Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate | 111230-51-4

• 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: Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate
• 英文别名: ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-5-nitro-4-oxoquinoline-3-carboxylate
• CAS: 111230-51-4
• 化学式: C₁₅H₁₁ClF₂N₂O₅
• 分子量: 372.713
• InChiKey: PPUPERUOTYGCFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  534.7±50.0 °C(Predicted)
• 密度：
  1.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate 在 RaNi 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 14.0h， 生成 5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic 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
• 作为产物：
  描述：

  ethyl 2-(3-chloro-2,4,5-trifluoro-6-nitro-benzoyl)-3-ethoxyacrylate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 9.5h， 生成 Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate
  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

• 4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial
  申请人：Warner-Lambert Company

  公开号：US04822801A1

  公开（公告）日：1989-04-18

  Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  描述了新型萘啉基、喹啉基和苯并噁嗪羧酸作为抗菌剂的小说，以及它们的制造、配方和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体的描述。
• 5-amino and 5-hydroxy-6-fluoroquinolones as antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04977154A1

  公开（公告）日：1990-12-11

  Novel 7-piperazine derivatives of 5-amino- and 5-hydroxy-1-cyclopropyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.

  本文介绍了一种新型的抗菌药物，即5-氨基和5-羟基-1-环丙基-1,4-二氢-4-氧喹诺酮-3-羧酸的七元哌嗪衍生物，以及它们的制备、配方和治疗细菌感染的方法。
• Antibacterial agents - II
  申请人：Warner-Lambert Company

  公开号：US05097032A1

  公开（公告）日：1992-03-17

  Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  本文描述了新型萘啶、喹啉和苯并噁嗪羧酸作为抗菌剂，以及其制备、配方和治疗细菌感染的使用方法，包括制备抗菌剂所使用的某些新型中间体的描述。
• 5-Amino and 5-hydroxy-6,8-difluoroquinolones as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0226961B1

  公开（公告）日：1991-06-12
• 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：——