2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester | 103772-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester
• 英文别名: ethyl 2,3,4,5-tetrafluoro-6-nitro-β-oxobenzenepropanoate；ethyl 2,3,4,5-tetrafluoro-6-nitrobenzoylacetate；2-nitro-3,4,5,6-tetrafluoro-β-oxo-benzene propanoic acid ethyl ester；2-Nitro-3,4,5,6-tetrafluoro-beta-oxobenzenepropanoic acid, ethyl ester；ethyl 3-oxo-3-(2,3,4,5-tetrafluoro-6-nitrophenyl)propanoate
• CAS: 103772-11-8
• 化学式: C₁₁H₇F₄NO₅
• 分子量: 309.174
• InChiKey: QBSOHVVDNJFEPR-UHFFFAOYSA-N

物化性质

• 沸点：
  381.0±37.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester 在 RaNi potassium tert-butylate 、 氢气 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 叔丁醇 为溶剂， 45.0~60.0 ℃ 、137.9 kPa 条件下， 反应 24.5h， 生成 1-环丙基-5-酰胺-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯
  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：

  2,3,4,5-四氟苯甲酸 在 正丁基锂 、 dipyridyl 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic 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

• 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。
• 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。
• Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acids; substituted-5-amino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0172651A1

  公开（公告）日：1986-02-26

  Novel naphthyridine-, quinoline- and benzoxazine carboxylic acids of formula or as antibacterial agents are described as well as methods for their manufacture and formulation. Also disclosed are certain novel intermediates used in the manufacture of the antibacterial agents.

  描述了新颖的式或作为抗菌剂的萘啶、喹啉和苯并噁嗪羧酸及其制造和配制方法。 此外，还公开了用于制造抗菌剂的某些新型中间体。
• Substituted-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids, derivatives thereof, pharmaceutical compositions comprising the compounds, and processes for producing the compounds
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0265230A1

  公开（公告）日：1988-04-27

  Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids of formula in which Z is are disclosed. The compounds are useful as antibacterial agents. Also disclosed is a process for producing the compounds and a pharmaceutical composition comprising the compounds.

  新颖的萘啶、喹啉和苯并噁嗪羧酸，其式为 其中 Z 为 的新型萘啶-喹啉-和苯并噁嗪羧酸。这些化合物可用作抗菌剂。还公开了生产这些化合物的工艺和包含这些化合物的药物组合物。
• 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