4-hydroxy-1-methyl-2-oxo-N-(thiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide | 84088-57-3

• 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: 4-hydroxy-1-methyl-2-oxo-N-(thiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide
• 英文别名: 4-hydroxy-1-methyl-2-oxo-N-(1,3-thiazol-2-yl)quinoline-3-carboxamide
• CAS: 84088-57-3
• 化学式: C₁₄H₁₁N₃O₃S
• 分子量: 301.326
• InChiKey: ATHHWTUOHYVOSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-hydroxy-1-methyl-2-oxo-N-(thiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  다이하이드로퀴놀린 카복스아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물

  摘要：

  二羟基喹诺啉羧酰胺衍生物或其药学上允许的盐作为有效成分，用于预防或治疗肺炎的药学组合物已经公开。该药学组合物不仅具有优异的抗菌活性，而且对于对传统抗生素如红霉素等常用抗菌剂具有药物耐药性的肺炎菌具有出色的抗菌活性，因此可以作为预防或治疗由这些肺炎菌引起的肺炎疾病的药学组合物而被有益地使用。

  公开号：

  KR20190067546A

文献信息

• Heterocyclic carboxamides, compositions containing such compounds,
  申请人：Aktiebolaget Leo

  公开号：US04547511A1

  公开（公告）日：1985-10-15

  This invention relates to novel heterocyclic carboxamides which increase the activity of the immune system and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds and methods of treatment therewith.

  本发明涉及一种新型杂环羧酰胺，其能够增强免疫系统的活性，以及其制备方法。本发明还涉及含有上述化合物的药物组合物和治疗方法。
• Discovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains
  作者：Srigouri Huddar、Chul Min Park、Hyung Jun Kim、Soojin Jang、Sunkyung Lee

  DOI：10.1016/j.bmcl.2020.127071

  日期：2020.5

  New therapies for treating drug-resistant pneumococcal infections are urgently needed. The novel scaffold 6hydroxy-4-oxo-1,2-dihydro-4H-quinoline was shown to have similar efficacies against all three different serotypes of S. pneumoniae, ATCC 49617 (TM) (19F), ATCC BAA-1663 (TM) (15B), and ATCC 700904 (TM) (19A), in a resazurin-based high-throughput screen using the Korea Chemical Bank library. Further studies to identify a new lead with this scaffold, including tricyclic pyrrolo[3,2,1-ij]quinolone and pyrido[3,2,1-ij]quinolone derivatives, led to the identification of 6d, 7d and 12a. Compound 6d (IC50 = 0.92, 0.75, and 0.77 mu M), 7d (IC50 = 0.57, 0.66, and 0.38 mu M) and 12a (IC50, = 0.27, 1.03, and 0.62 mu M) showed submicromolar IC50, values against 19F, 15B, and 19A, respectively, and thus serve as a starting point for further optimization. While some of compounds in this series exhibited acceptable pharmacokinetic profiles in preliminary in vivo rat experiments, the most active compound 12a showed poor solubility and high plasma protein binding. Our current research efforts are focused on optimizing compounds to improve physicochemical properties as well as potency.
• 4-Hydroxy-2-quinolones. 23. N-(2-thiazolyl)amides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids ? A new group of potential antiinflammatory agents
  作者：I. V. Ukrainets、O. V. Gorokhova、S. G. Taran、A. V. Turov

  DOI：10.1007/bf01184887

  日期：1994.10
• Heterocyclic carboxamides, compositions containing such compounds, processes for their preparation and methods of treatment therewith
  申请人：AB LEO

  公开号：EP0059698B1

  公开（公告）日：1985-09-25
• US4547511A
  申请人：——

  公开号：US4547511A

  公开（公告）日：1985-10-15