5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid | 111230-53-6

• 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-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid；5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid；1-cyclopropyl-5-amino-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• CAS: 111230-53-6
• 化学式: C₁₃H₉ClF₂N₂O₃
• 分子量: 314.676
• InChiKey: WIQKAXGONOSOST-UHFFFAOYSA-N

物化性质

• 熔点：
  285-291 °C
• 沸点：
  543.4±50.0 °C(Predicted)
• 密度：
  1.778±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 以48.8%的产率得到1-Cyclopropyl-5-amino-8-chloro-6-fluoro-1,4-dihydro-7-(cis-3-methylamino-4-methoxy-1-pyrrolidinyl)-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Quinolinecarboxylic acids

  摘要：

  化合物的名称为新奎诺酸类似物，化学式为：##STR1## 其中R.sup.1为C.sub.1-C.sub.4烷基，R.sup.2和R.sup.3分别为相同或不同的氢或C.sub.1-C.sub.4烷基，R.sup.4为环丙基，苯基，卤代苯基或噻吩基，可选用C.sub.1-C.sub.4烷基或卤素取代，R.sup.5为卤素，或其药学上可接受的盐，具有比已知类似物更强和更持久的抗G(+)和G(-)细菌活性，可用作口服剂量为1-500毫克的抗菌剂，成人每天最好为50-100毫克。

  公开号：

  US05106854A1
• 作为产物：
  描述：

  3-氯-2,4,5-三氟苯甲酸 在 RaNi 盐酸 、 正丁基锂 、 dipyridyl 、 草酰氯 、 硫酸 、 potassium tert-butylate 、 氢气 、 硝酸 、 乙酸酐 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， -70.0~70.0 ℃ 、137.9 kPa 条件下， 反应 49.0h， 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

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.

  本发明涉及7-哌嗪衍生物的新型抗菌剂，其基础结构为5-氨基-和5-羟基-1-环丙基-1,4-二氢-4-氧喹啉-3-羧酸，并描述了它们的制备方法、配方和用于治疗细菌感染的用途。
• 5-aminoquinolone carboxylic acid derivative and antibacterial agent
  申请人：SS Pharmaceutical Co., Ltd.

  公开号：US05430028A1

  公开（公告）日：1995-07-04

  A 5-aminoquinolone carboxylic acid derivative represented by the following general formula (1): ##STR1## wherein R.sup.1 means a hydrogen atom, an amino group, a linear or branched alkyl group having 1-5 carbon atoms and an alkylamino group containing a linear or branched alkyl group having 1-5 carbon atoms, R.sup.2 denotes a hydrogen atom or a linear or branched alkyl group having 1-5 carbon atoms, X stands for a halogen atom, Y means CH.sub.2, NH, CHR.sup.3 NR.sup.3, (R.sup.3 denoting a linear or branched alkyl group having 1-5 carbon atoms) or an oxygen atom, and Z stands for an oxygen atom or 2 hydrogen atoms, or a salt thereof, and an antibacterial agent containing such a derivative or salt as an active ingredient. The derivative or salt thereof exhibits strong anti-bacterial activities against Grampositive bacteria including tolerant bacteria, and is satisfactorily absorbed in a living body.

  以下是一种由5-氨基喹啉羧酸衍生物表示的通式（1）：##STR1## 其中，R1表示氢原子、氨基、具有1-5个碳原子的线性或支链烷基和含有1-5个碳原子的线性或支链烷基的烷基氨基基团，R2表示氢原子或具有1-5个碳原子的线性或支链烷基，X代表卤素原子，Y表示CH2、NH、CHR3NR3（其中R3表示具有1-5个碳原子的线性或支链烷基）或氧原子，Z代表氧原子或2个氢原子，或其盐。该衍生物或其盐对包括耐药菌在内的革兰氏阳性菌表现出强烈的抗菌活性，并且在生物体内能够被满意吸收。
• 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。