ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate | 107564-02-3

• 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 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate
• 英文别名: 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester；Ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate；ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4-oxoquinoline-3-carboxylate
• CAS: 107564-02-3
• 化学式: C₁₅H₁₁F₄NO₃
• 分子量: 329.251
• InChiKey: HHBWJFABYNBJCG-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  430.4±45.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate 在 palladium on activated charcoal 吡啶 、 硫酸 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 1.84h， 生成 sparfloxacin
  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 3-cyclopropylamino-2-pentafluorobenzoyl acrylate 在 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 18.0h， 以91.5%的产率得到ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  [EN] PROCESSES FOR PREPARING QUINOLONECARBOXYLATE DERIVATIVES
  [FR] PROCEDE DE PREPARATION DE DERIVES DE QUINOLONECARBOXYLATE

  摘要：

  本发明提供了一种在温和条件下以高收率制备喹诺酮羧酸酯衍生物的方法，从而有利于其大规模量产的应用。

  公开号：

  WO2004056781A1

文献信息

• [EN] QUINOLIN-4-ONE AND 4(1H)-CINNOLINONE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE QUINOLIN-4-ONE ET DE 4(1H)-CINNOLINONE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：FREQUENCY THERAPEUTICS INC

  公开号：WO2020163816A1

  公开（公告）日：2020-08-13

  The present disclosure relates to quinolin-4-one and 4(1H)-cinnolinone compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.

  本公开涉及喹啉-4-酮和4(1H)-喹啉酮化合物，以及使用它们诱导干/祖细胞支持细胞自我更新的方法，包括诱导干/祖细胞增殖，同时在子细胞中保持分化为组织细胞的能力。
• 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。
• Aminoquinolones as GSK-3 inhibitors
  申请人：Cociorva Oana

  公开号：US20070254866A1

  公开（公告）日：2007-11-01

  Provided herein are aminoquinolones and pharmaceutically acceptable derivatives thereof. In certain embodiments, provided herein are compounds, compositions and methods for treating, preventing or ameliorating GSK-3 mediated diseases.

  本文提供了氨基喹啉及其药用可接受的衍生物。在某些实施例中，本文提供了用于治疗、预防或改善GSK-3介导疾病的化合物、组合物和方法。
• Quinolone derivatives and salts thereof, preparation processes thereof,
  申请人：Wakunaga Seiyaku Kabushiki Kaisha

  公开号：US05153203A1

  公开（公告）日：1992-10-06

  Antibacterial quinolone derivatives represented by the following formula and salts thereof are disclosed. ##STR1## wherein R.sup.1 meawns a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted phenyl group, R.sup.2 denotes a hydrogen atom or a carboxyl-protecting group, R.sup.3 represents a hydrogen or halogen atom or an amino, mono- or di-(lower alkyl)amino, hydroxyl or lower alkoxyl group, X is a hydrogen or halogen atom, Y means a nitrogen atom or a group C-R.sup.4 in which R.sup.4 is a hydrogen or halogen atom or a lower alkyl or lower alkoxyl group or is a group ##STR2## which forms a ring together with R.sup.1 (i.e., the asterisked carbon atoms are linked to the N(1) atom of the quinolone skeleton), and A denotes a specific N-containing group. Preparation processes of the quinolone derivatives and antibacterial agents containing the same are also disclosed.

  抗菌喹诺酮衍生物及其盐的化学式如下所示。其中，R.sup.1表示取代或未取代的较低烷基基团，取代或未取代的环烷基基团，取代或未取代的较低烯基基团或取代或未取代的苯基基团，R.sup.2表示氢原子或羧基保护基团，R.sup.3表示氢或卤素原子或氨基、单或双-(较低烷基)氨基、羟基或较低烷氧基基团，X是氢或卤素原子，Y表示氮原子或C-R.sup.4基团，其中R.sup.4是氢或卤素原子或较低烷基或较低烷氧基团或是一个组合成环的基团，形成一个环与R.sup.1一起（即星号标记的碳原子与喹诺酮骨架的N(1)原子相连），A表示特定的含氮基团。还披露了喹诺酮衍生物的制备方法和含有它们的抗菌剂。
• 7-substituted-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid
  申请人：SynPhar Laboratories, Inc.

  公开号：US05342846A1

  公开（公告）日：1994-08-30

  Substituted quinoline compounds and intermediates thereto, processes for producing those compounds and intermediates, pharmaceutical compositions using those compounds, methods for treating bacterial infections using those compounds, and methods for disinfecting using those compounds.

  取代喹啉化合物及其中间体，生产这些化合物和中间体的过程，使用这些化合物的药物组合物，使用这些化合物治疗细菌感染的方法，以及使用这些化合物进行消毒的方法。