ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate | 74011-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate
• 英文别名: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester；Ethyl 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate；ethyl 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylate
• CAS: 74011-30-6
• 化学式: C₁₇H₂₁FN₄O₃
• 分子量: 348.377
• InChiKey: KCOXGCQZFDAHFC-UHFFFAOYSA-N

物化性质

• 沸点：
  551.4±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate 在 盐酸 作用下， 反应 1.0h， 以90%的产率得到enoxacin hydrochloride
  参考文献：
  名称：

  通过balz-schiemann反应合成氟化吡啶。新型抗菌性吡啶酮羧酸依诺沙星的替代途径†

  摘要：

  描述了通过Balz-Schiemann反应对2，6-二取代的3-氨基吡啶5和12的氟化。2,6-二氯-3- pyridinediazonium四氟硼酸盐（6）和2-取代的6-乙酰氨基-3- pyridinediazonium四氟硼酸盐13用或不用溶剂加热，得到相应的氟化吡啶7和14分别，以良好产率。通过已知方法将2-取代的6-乙酰氨基-3-氟吡啶（14）转化为一系列的7-取代的1-乙基-6-氟-1,4-二氢-4-氧代-1,8-萘啶- 3-羧酸21包括新的潜在抗菌剂依诺沙星[1-乙基-6-氟-1,4-二氢-4-氧代-7-（1-哌嗪基）-1,8-萘啶-3-羧酸[（2）] 。

  DOI：

  10.1002/jhet.5570210309
• 作为产物：
  描述：

  ethyl 7-(ethylthio)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 在 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 6.5h， 生成 ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  通过balz-schiemann反应合成氟化吡啶。新型抗菌性吡啶酮羧酸依诺沙星的替代途径†

  摘要：

  描述了通过Balz-Schiemann反应对2，6-二取代的3-氨基吡啶5和12的氟化。2,6-二氯-3- pyridinediazonium四氟硼酸盐（6）和2-取代的6-乙酰氨基-3- pyridinediazonium四氟硼酸盐13用或不用溶剂加热，得到相应的氟化吡啶7和14分别，以良好产率。通过已知方法将2-取代的6-乙酰氨基-3-氟吡啶（14）转化为一系列的7-取代的1-乙基-6-氟-1,4-二氢-4-氧代-1,8-萘啶- 3-羧酸21包括新的潜在抗菌剂依诺沙星[1-乙基-6-氟-1,4-二氢-4-氧代-7-（1-哌嗪基）-1,8-萘啶-3-羧酸[（2）] 。

  DOI：

  10.1002/jhet.5570210309

文献信息

• Substituted quinoline carboxylic acid derivatives
  申请人：Kyorin Seiyaku Kabushiki Kaisha

  公开号：US04448962A1

  公开（公告）日：1984-05-15

  This invention relates to new compounds of value as antibacterial agents. More particularly, it relates to quinoline carboxylic acid derivatives, the hydrates and the acid or alkali addition salts thereof.

  这项发明涉及作为抗菌剂有价值的新化合物。更具体地说，它涉及喹啉羧酸衍生物，以及其水合物和酸性或碱性加盐。
• Hybrid Antibacterials. DNA Polymerase−Topoisomerase Inhibitors
  作者：Chengxin Zhi、Zheng-yu Long、Andrzej Manikowski、Jeanne Comstock、Wei-Chu Xu、Neal C. Brown、Paul M. Tarantino,、Karsten A. Holm、Edward J. Dix、George E. Wright、Marjorie H. Barnes、Michelle M. Butler、Kimberly A. Foster、William A. LaMarr、Benoit Bachand、Richard Bethell、Caroline Cadilhac、Sylvie Charron、Serge Lamothe、Irina Motorina、Richard Storer

  DOI：10.1021/jm0510023

  日期：2006.2.1

  Novel Gram-positive (Gram+) antibacterial compounds consisting of a DNA polymerase IIIC (pol IIIC) inhibitor covalently connected to a topoisomerase/gyrase inhibitor are described. Specifically, 3-substituted 6-(3-ethyl-4-methylanilino)uracils (EMAUs) in which the 3-substituent is a fluoroquinolone moiety (FQ) connected by various linkers were synthesized. The resulting "AU-FQ" hybrid compounds were significantly more potent than the parent EMAU compounds as inhibitors of pol IIIC and were up to 64-fold more potent as antibacterials in vitro against Gram+ bacteria. The hybrids inhibited the FQ targets, topoisomerase IV and gyrase, with potencies similar to norfloxacin but 10-fold lower than newer agents, for example, ciprofloxacin and sparfloxacin. Representative hybrids protected mice from lethal Staphylococcus aureus infection after intravenous dosing, and one compound showed protective effect against several antibiotic-sensitive and -resistant Gram+ infections in mice. The AU-FQ hybrids are a promising new family of antibacterials for treatment of antibiotic-resistant Gram+ infections.
• Novel naphtyridine derivatives and pharmaceutical compositions containing them
  申请人：Société anonyme dite: LABORATOIRE ROGER BELLON

  公开号：EP0009425B1

  公开（公告）日：1982-01-27
• MATSUMOTO, DZYUNITI;TAKAERI, JOSIYUKI;NISIMURA, JOSIRO
  作者：MATSUMOTO, DZYUNITI、TAKAERI, JOSIYUKI、NISIMURA, JOSIRO

  DOI：——

  日期：——
• MATSUMOTO, JUN-ICHI;MIYAMOTO, TERUYUKI;MINAMIDA, AKIRA;NISHIMURA, YOSHIRO+, J. HETEROCYCL. CHEM., 1984, 21, N 3, 673-679
  作者：MATSUMOTO, JUN-ICHI、MIYAMOTO, TERUYUKI、MINAMIDA, AKIRA、NISHIMURA, YOSHIRO+

  DOI：——

  日期：——