1-(4'-fluoro-phenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester | 98105-80-7

• 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-(4'-fluoro-phenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester
• 英文别名: 7-chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester；7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester；ethyl 7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylate
• CAS: 98105-80-7
• 化学式: C₁₈H₁₂ClF₂NO₃
• 分子量: 363.748
• InChiKey: JLDJEPINTWDIOY-UHFFFAOYSA-N

物化性质

• 沸点：
  497.4±45.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4'-fluoro-phenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 29.5h， 生成 沙拉沙星
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003
• 作为产物：
  描述：

  2,4-二氯-5-氟-Β-氧代苯丙酸乙酯 在 乙酸酐 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-(4'-fluoro-phenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003

文献信息

• 7-(substituted)piperaziny
  申请人：American Cyanamid Company

  公开号：US04940710A1

  公开（公告）日：1990-07-10

  7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.

  7-(取代)哌嗪基-1-乙基-6-氟-4-氧代-3-喹啉羧酸，其药理上可接受的盐，含有它们的组合物，生产它们的过程和中间体，以及使用它们治疗温血动物细菌感染的方法。
• Piperazine derivatives
  申请人：American Cyanamid Company

  公开号：US05210193A1

  公开（公告）日：1993-05-11

  7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.

  7-(取代)piperazinyl-1-乙基-6-氟-4-氧代-3-喹啉羧酸及其药理学上可接受的盐，含有它们的组合物，生产它们的过程和中间体以及使用它们治疗温血动物细菌感染的方法。
• Utilisation du fluorure de tetrabutylammonium comme de cyclisation dans la synthese d'antibacterines derives d'acide pyridone-4-carboxylique-3
  作者：D. Bouzard、P. Di Cesare、M. Essiz、J.P. Jacquet、P. Remuzon

  DOI：10.1016/s0040-4039(00)82082-1

  日期：1988.1
• WENTLAND, MARK P.
  作者：WENTLAND, MARK P.

  DOI：——

  日期：——
• BOUZARD, D.;DI, CESARE P.;ESSIZ, M.;JACQUET, J. P.;REMUZON, P., TETRAHEDRON LETT., 29,(1988) N 16, 1931-1934
  作者：BOUZARD, D.、DI, CESARE P.、ESSIZ, M.、JACQUET, J. P.、REMUZON, P.

  DOI：——

  日期：——