5-amino-7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid | 115904-58-0

• 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-amino-7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 5-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 115904-58-0
• 化学式: C₁₇H₁₈ClFN₄O₃
• 分子量: 380.806
• InChiKey: YTVOXFQCURQYHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-氯-2,4,5-三氟-6-硝基苯甲酸 在 RaNi 盐酸 、 正丁基锂 、 dipyridyl 、 草酰氯 、 potassium tert-butylate 、 氢气 、 乙酸酐 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， -70.0~60.0 ℃ 、137.9 kPa 条件下， 反应 43.5h， 生成 5-amino-7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-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

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-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。
• Bisphosphonate quinolone conjugates and uses thereof
  申请人：BIOVINC, LLC

  公开号：US10865220B2

  公开（公告）日：2020-12-15

  Described herein are bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof that can include a bisphosphonate and a quinolone, where the quinolone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof.

  本文描述的是双膦酸盐喹诺酮化合物、共轭物及其药物制剂，可包括双膦酸盐和喹诺酮，其中喹诺酮可与双膦酸盐可释放地偶联。本文还提供了制造和使用双膦酸盐喹诺酮化合物、共轭物及其药物制剂的方法。
• Improved process for the preparation of 5-amino-7-(substituted amino)-quinoline-3-carboxylic acids
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0342649B1

  公开（公告）日：1994-11-30