3-ethylaminoazetidine | 318269-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 3-ethylaminoazetidine
• 英文别名: N-ethylazetidin-3-amine
• CAS: 318269-51-1
• 化学式: C₅H₁₂N₂
• mdl: MFCD19216591
• 分子量: 100.164
• InChiKey: QLBGCEBVDMZPPN-UHFFFAOYSA-N

物化性质

• 沸点：
  147.2±8.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethylaminoazetidine 、 1-(5-amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到1-(5-Amino-2,4-difluorophenyl)-8-chloro-7-[3-(ethylamino)azetidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  A Novel Antibacterial 8-Chloroquinolone with a Distorted Orientation of the N1-(5-Amino-2,4-difluorophenyl) Group

  摘要：

  Fluoroquinolones represent a major class of antibacterial agents with great therapeutic potential. In this study, we designed m-aminophenyl groups as novel N-1 substituents of naphthyridones and quinolones. Among newly synthesized compounds, 7-(3-aminoazetidin-1-yl)-1-(5-amino-2,4-difluorophenyl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (4) has extremely potent antibacterial activities against Gram (+) as well as Gram (-) bacteria. This compound is significantly more potent than trovafloxacin against clinical isolates: 30 times against Streptococcus pneumoniae and 128 times against methicillin resistant Staphylococcus aureus. The structure-activity relationship (SAR) study revealed that a limited combination of 1-(5-amino-2,4-difluorophenyl) group, 7-(azetidin-1-yl) group, and 8-Cl atom (or Br atom or Me group) gave potent antibacterial activity. An X-ray crystallographic study of a 7-(3-ethylaminoazetidin-1-yl)-8-chloro derivative demonstrated that the N-1 aromatic group was remarkably distorted out of the core quinolone plane by steric repulsion between the C-8 C1 atom and the N-1 substituent. Furthermore, a molecular modeling study of 4 and its analogues demonstrated that a highly distorted orientation was induced by a steric hindrance of the C-8 substituent, such as Cl, Br, or a methyl group. Thus, their highly strained conformation should be a key factor for the potent antibacterial activity.

  DOI：

  10.1021/jm0205090

文献信息

• Quinolinecarboxylic acid derivative or salts thereof
  申请人：Yazaki Akira

  公开号：US06858625B1

  公开（公告）日：2005-02-22

  This invention relates to 1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-7-(3-ethylaminoazetidin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or a salt thereof, and also to a medicine containing the same. This compound has characteristic features that, when administered orally, it has extremely high blood half-life and bioavailability while retaining properties that it has extremely high antimicrobial effects and has low toxicity. It can be used widely as preventives, therapeutics and the like for various infectious diseases of human and animals.

  本发明涉及1-(6-氨基-3,5-二氟吡啶-2-基)-8-溴-7-(3-乙基氨基氮杂环戊烷-1-基)-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸或其盐，并且涉及含有该化合物的药物。该化合物具有特征性特点，当口服时，具有极高的血液半衰期和生物利用度，同时保持极高的抗微生物效果和低毒性。它可以广泛用于人类和动物的各种传染病的预防、治疗等。
• QUINOLINECARBOXYLIC ACID DERIVATIVE OR SALTS THEREOF
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP1193266B1

  公开（公告）日：2003-08-27