ethyl 7-[(4S)-4-amino-3,3-dimethylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate | 1025875-02-8

• 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 7-[(4S)-4-amino-3,3-dimethylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 1025875-02-8
• 化学式: C₂₁H₂₉FN₄O₃
• 分子量: 404.485
• InChiKey: JXHHGVSDAVGQGE-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 7-[(4S)-4-amino-3,3-dimethylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate 在 sodium hydroxide 作用下， 生成 7-[(4S)-4-amino-3,3-dimethylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028
• 作为产物：
  描述：

  (2R)-(-)-3,3-dimethylbutane-1,2,4-triol 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium azide 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 74.34h， 生成 ethyl 7-[(4S)-4-amino-3,3-dimethylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028