ethyl 5-amino-1-ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate | 836621-26-2

• 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-amino-1-ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: Ethyl 5-amino-1-ethyl-6,7-difluoro-4-oxoquinoline-3-carboxylate
• CAS: 836621-26-2
• 化学式: C₁₄H₁₄F₂N₂O₃
• 分子量: 296.274
• InChiKey: DUWDFAZQUYERGW-UHFFFAOYSA-N

物化性质

• 沸点：
  460.1±45.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-1-ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 5-Amino-1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic 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
• 作为产物：
  描述：

  2,3,4,6-四氟苯甲酸 在 RaNi 4-二甲氨基吡啶 、 sodium hydroxide 、 草酰氯 、 硫酸 、 potassium tert-butylate 、 氢气 、 乙酸酐 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 45.0~60.0 ℃ 、137.9 kPa 条件下， 反应 182.5h， 生成 ethyl 5-amino-1-ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
  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

• [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。
• Quinolone derivative or salt thereof
  申请人：Watanuki Susumu

  公开号：US20060148806A1

  公开（公告）日：2006-07-06

  A platelet aggregation inhibitor comprising a quinolone derivative or a pharmaceutically acceptable salt thereof as an active ingredient, and a novel quinolone derivative or a pharmaceutically acceptable salt thereof useful as a platelet aggregation inhibitor.

  一种血小板聚集抑制剂，其活性成分为喹诺酮衍生物或其药学上可接受的盐，以及一种新型喹诺酮衍生物或其药学上可接受的盐，可用作血小板聚集抑制剂。
• QUINOLONE DERIVATIVE OR SALT THEREOF
  申请人：WATANUKI Susumu

  公开号：US20090124617A1

  公开（公告）日：2009-05-14

  A platelet aggregation inhibitor comprising a quinolone derivative or a pharmaceutically acceptable salt thereof as an active ingredient, and a novel quinolone derivative or a pharmaceutically acceptable salt thereof useful as a platelet aggregation inhibitor.

  一种血小板聚集抑制剂，包括喹诺酮衍生物或其药学上可接受的盐作为活性成分，以及一种新型喹诺酮衍生物或其药学上可接受的盐，可用作血小板聚集抑制剂。
• EP1650192
  申请人：——

  公开号：——

  公开（公告）日：——
• US7488739B2
  申请人：——

  公开号：US7488739B2

  公开（公告）日：2009-02-10