cis-(3S,4S)-3-amino-4-methylpyrrolidine dihydrochloride | 114214-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: cis-(3S,4S)-3-amino-4-methylpyrrolidine dihydrochloride
• 英文别名: (3S,4S)-3-amino-4-methylpyrrolidine dihydrochloride
• CAS: 114214-74-3；132920-87-7；141449-84-5；144124-90-3；144124-91-4
• 化学式: C₅H₁₂N₂*2ClH
• 分子量: 173.086
• InChiKey: VGUPEMDWSCTWNF-UYXJWNHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.05
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-(3S,4S)-3-amino-4-methylpyrrolidine dihydrochloride 在 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 (3S,4S)-7-(3-amino-4-methylpyrrolidinyl)-1-(1,1-dimethylethyl)-1,4-dihydro-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：

  [(3R,4S)-1-benzyl-4-methylpyrrolidin-3-yl] 4-methylbenzenesulfonate 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.5h， 生成 cis-(3S,4S)-3-amino-4-methylpyrrolidine dihydrochloride
  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

文献信息

• QUINOLONE DERIVATIVE OR SALT THEREOF, AND ANTIBACTERIAL CONTAINING THE SAME
  申请人：WAKUNAGA SEIYAKU KABUSHIKI KAISHA

  公开号：EP0700912A1

  公开（公告）日：1996-03-13

  A quinolone derivative represented by general formula (1) or a salt thereof, and an antibacterial containing the same, wherein R¹ represents isoxazolyl or isothiazolyl each of which may be substituted; R² represents hydrogen, halogen, lower alkyl, hydroxy, amino or nitro; R³ represents hydrogen or halogen; and Y represents halogen, optionally substituted saturated cyclic amino or H₂N-(CH₂)m-A-. This compound is useful as an antibacterial, can be used as medicines for humans and animals, drugs for fishes, pesticides and food preservative, and is expected to have an anti-HIV activity.

  一种喹诺酮衍生物，其由通式(1)或其盐表示，以及含有该衍生物的抗菌剂，其中R¹表示可被取代的异噁唑基或异噻唑基；R²表示氢、卤素、低级烷基、羟基、氨基或硝基；R³表示氢或卤素；Y表示卤素、可被取代的饱和环状氨基或H₂N-(CH₂)m-A-。该化合物作为抗菌剂具有实用性，可用于人畜药物、鱼类药物、农药及食品防腐剂，并预期具有抗HIV活性。