ethyl 5-(benzyloxy)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate | 114008-14-9

• 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: ethyl 5-(benzyloxy)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate
• 英文别名: Ethyl 1-cyclopropyl-6,7,8-trifluoro-4-oxo-5-phenylmethoxyquinoline-3-carboxylate
• CAS: 114008-14-9
• 化学式: C₂₂H₁₈F₃NO₄
• 分子量: 417.384
• InChiKey: CEGCUXHGUNWUHC-UHFFFAOYSA-N

物化性质

• 沸点：
  558.8±50.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 5-(benzyloxy)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate 在 硫酸 、 溶剂黄146 作用下， 反应 0.17h， 以92%的产率得到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
• 作为产物：
  描述：

  ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate 、 苯甲醇 生成 ethyl 5-(benzyloxy)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  MIYAMOTO, KOSI;KATAOKA, MASAXIRO;NAKANO, DZYUNDZI;MATSUMOTO, DZYUNITI;NAK+

  摘要：

  DOI：

文献信息

• MIYAMOTO, TERUYUKI;MATSUMOTO, JUN-ICHI;CHIBA, KATSUMI;EGAWA, HIROSHI;SHIB+, J. MED. CNEM., 33,(1990) N, C. 1645-1656
  作者：MIYAMOTO, TERUYUKI、MATSUMOTO, JUN-ICHI、CHIBA, KATSUMI、EGAWA, HIROSHI、SHIB+

  DOI：——

  日期：——
• JPS62226962A
  申请人：——

  公开号：JPS62226962A

  公开（公告）日：1987-10-05