1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid | 114008-16-1

• 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: 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 5-hydroxy-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-hydroxy-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-6,7,8-trifluoro-5-hydroxy-4-oxoquinoline-3-carboxylic acid
• CAS: 114008-16-1
• 化学式: C₁₃H₈F₃NO₄
• 分子量: 299.206
• InChiKey: RRSXXLZPDQRYEU-UHFFFAOYSA-N

物化性质

• 熔点：
  218 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  506.2±50.0 °C(Predicted)
• 密度：
  1.809±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  77.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid 生成 1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-hydroxy-7-(4-hydroxyimino-1-piperidinyl)-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Oxime derivatives

  摘要：

  一种公式为：##STR1##的肟衍生物，其中R是氢原子或C.sub.1-5烷基基团，R.sub.1是氢原子、C.sub.1-5烷基基团或羧基保护基团，R.sub.2是氢原子、卤素原子、羟基或氨基，R.sub.3是C.sub.3-7环烷基基团，R.sub.4是氢原子、卤素原子或C.sub.1-4烷氧基团，R.sub.5和R.sub.6中的每一个可能相同或不同，是氢原子或C.sub.1-5烷基基团，或者R.sub.5和R.sub.6一起表示一个C.sub.2-4烷基基团，与相邻的碳原子一起形成一个C.sub.3-5环，前提是当R.sub.2是氢原子时，R.sub.4是C.sub.1-4烷氧基团，m是0或1的整数，n是1到3的整数；或其药学上可接受的盐。

  公开号：

  US05276041A1
• 作为产物：
  描述：

  ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate 在 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 1.17h， 生成 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Pyridonecarboxylic acids as antibacterial agents. Part 14. Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency

  摘要：

  A series of 5,7-disubstituted 1-cyclopropyl-6,8-difluoro-4(1H)-oxoquinoline-3-carboxylic acids (10-36) were prepared; the C-5 substituent in these compounds comprised halo, hydroxy, mercapto, and amino groups and the C-7 functional group included variously substituted piperazines. In vitro antibacterial screening results indicated that the amino group was optimal among the C-5 substituents. A combination of the C-5 amino group and the C-7 3,5-dimethylpiperazinyl appendage in this series conferred the best overall antibacterial property with lack of adverse drug interactions. Compound 36k [named sparfloxacin, originally AT-4140, 5-amino-1-cyclopropyl-6,8-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)- 4(1H)-oxoquinoline-3-carboxylic acid] was superior to ciprofloxacin in both in vitro and in vivo potency and hence was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00168a018

文献信息

• Pyridonecarboxylic acid antibacterial agents. Part XV. Synthesis of 7-thio-substituted 4-oxoquinoline-3-carboxylic acids with antibacterial activity.
  作者：Yoshiro NISHIMURA、Tohru HIROSE、Hidetsugu OKADA、Koh-ichiro SHIBAMORI、Junji NAKANO、Jun-ichi MATSUMOTO

  DOI：10.1248/cpb.38.2190

  日期：——

  A series of C-7 thio-substituted 1-cyclopropyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids were prepared and tested for their antibacterial activity. Structure-activity relationships associated with the C-5 and C-7 substituents were discussed. Among the C-7 substituents including alkylthio, arylthio, heteroarylthio, and cyclic aminothio groups, a 2-aminoethylthio group was the best for enhancing in vitro antibacterial activity. The C-5 variants increased activity in the order OH

  制备并测试了一系列 C-7 硫代 1-环丙基-1，4-二氢-4-氧代喹啉-3-羧酸的抗菌活性。讨论了与 C-5 和 C-7 取代基相关的结构-活性关系。在 C-7 取代基（包括烷基硫代、芳基硫代、杂芳基硫代和环状硫代氨基）中，2-氨基乙基硫代最能提高体外抗菌活性。C-5 变体提高活性的顺序为 OH喹啉-3-羧酸（18）的活性最高。
• 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.

  本文介绍了新型萘啶、喹啉和苯并噁嗪羧酸作为抗菌剂，以及它们的制备、配方和用于治疗细菌感染的方法，包括用于制备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。
• 7-Isoindolinyl-chinolon- und naphthyridoncarbonsäure-Derivate
  申请人：BAYER AG

  公开号：EP0520240A1

  公开（公告）日：1992-12-30

  Die Erfindung betrifft neue Chinolon- und Naphthyridoncarbonsäure-Derivate, die in 7-Stellung durch einen partiell hydrierten Isoindolinylring substituiert sind, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel und Futterzusatzstoffe.

  本发明涉及在 7 位被部分氢化的异吲哚啉基环取代的新型喹诺酮和萘啶酮羧酸衍生物、其制备工艺以及含有这些衍生物的抗菌剂和饲料添加剂。