1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid | 124487-36-1

• 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-difluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 1-cyclopropyl-6,7-difluoro-5-hydroxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid；1-Cyclopropyl-6,7-difluoro-5-hydroxy-4-oxoquinoline-3-carboxylic acid
• CAS: 124487-36-1
• 化学式: C₁₃H₉F₂NO₄
• 分子量: 281.216
• InChiKey: VTJUHZVOJCXDEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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：
  7

反应信息

• 作为反应物：
  描述：

  7-(1-tert-butoxycarbonylaminomethyl-2-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 、 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-hydroxy-4-oxo-3-quinolinecarboxylic acid 在 盐酸 作用下， 生成 7-(1-aminomethyl-2-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride
  参考文献：
  名称：

  Use of 7-(1-aminomethyl-2-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)-quinolone carboxylic acid and naphthyridone carboxylic acid derivatives for treating Helicobacter pylori infections and the gastroduodenal diseases associated therewith

  摘要：

  该发明涉及使用在位置7被1-氨基甲基-2-氧-7-氮代双环[3.3.0]辛-7-基取代的喹诺酮和萘啶酮羧酸衍生物，以及它们的盐用于治疗幽门螺杆菌感染和相关的胃十二指肠疾病。

  公开号：

  US06288081B1
• 作为产物：
  描述：

  ethyl 3-oxo-3-(3,4,6-trifluoro-2-methoxyphenyl)propanoate 在 RaNi 盐酸 、 potassium tert-butylate 、 氢气 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 45.0~60.0 ℃ 、137.9 kPa 条件下， 反应 26.5h， 生成 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-hydroxy-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

• Use of 7-(1-aminomethyl-2-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)-quinolonecarboxylic acid and -naphthyridonecarboxylic acid derivatives for the therapy of Helicobacter pylori infections and associated gastroduodenal disorders
  申请人：——

  公开号：US20010036941A1

  公开（公告）日：2001-11-01

  The invention relates to the use of quinolone- and naphthyridonecarboxylic acid derivatives which are substituted in position 7 by a 1-aninomethyl-2-oxa-7-azabicyclo[3.3.0]oct-7-yl radical, and of their salts for the therapy of Helicobacter pylori infections and associated gastroduodenal disorders.

  本发明涉及使用在第7位被1-氨甲基-2-氧杂-7-氮杂双环[3.3.0]辛-7-基基团取代的喹诺酮和萘啶酮羧酸衍生物及其盐，用于治疗幽门螺杆菌感染和相关的胃十二指肠疾病。
• HAKAHO, DZYUNDZI;OKATA, XIDEHTSUGI;XIROSEH, TORU;MATSUMOTO, DZYUNITI;NAKA+
  作者：HAKAHO, DZYUNDZI、OKATA, XIDEHTSUGI、XIROSEH, TORU、MATSUMOTO, DZYUNITI、NAKA+

  DOI：——

  日期：——
• 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：——
• 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：EP0265230B1

  公开（公告）日：1992-01-08
• VERWENDUNG VON 7-(1-AMINOMETHYL-2-OXA-7-AZA-BICYCLO 3.3.0]OCT-7-YL)-CHINOLONCARBONSÄURE- UND -NAPHTHYRIDONCARBONSÄURE-DERIVATEN ZUR THERAPIE VON HELICOBACTER-PYLORI-INFEKTIONEN UND DEN DAMIT ASSOZIIERTEN GASTRODUODENALEN ERKRANKUNGEN
  申请人：BAYER AG

  公开号：EP0944385B1

  公开（公告）日：2002-10-16