N-{(5S)-3-[4-(Azetidin-3-yloxy)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl)-acetamide | 790702-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-{(5S)-3-[4-(Azetidin-3-yloxy)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl)-acetamide
• 英文别名: N-[[(5S)-3-[4-(azetidin-3-yloxy)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 790702-35-1
• 化学式: C₁₅H₁₈FN₃O₄
• 分子量: 323.324
• InChiKey: HMHMNBMTWYIFBQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  环丙基萘啶羧酸 、 N-{(5S)-3-[4-(Azetidin-3-yloxy)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl)-acetamide 在 三甲基氯硅烷 、 TEA 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 7-[3-[4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenoxy]azetidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Structure–activity relationship in the oxazolidinone–quinolone hybrid series: influence of the central spacer on the antibacterial activity and the mode of action

  摘要：

  Oxazolidinone-quinolone hybrids, which combine the pharmacophores of a quinolone and an oxazolidinone, were synthesised and shown to be active against a variety of susceptible and resistant Gram-positive and Gram-negative bacteria. The nature of the spacer greatly influences the antibacterial activity by directing the mode of action, that is quinotone- and/or oxazolidinone-like activity. The best compounds in this series have a balanced dual mode of action and overcome all types of resistance, including resistance to quinolones and linezolid, in clinically relevant Gram-positive pathogens. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.028
• 作为产物：
  描述：

  3,4-二氟硝基苯 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 sodium azide 、 TEA 、 水 、 氢气 、 sodium hydride 、 碳酸氢钠 、 溶剂黄146 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 N-{(5S)-3-[4-(Azetidin-3-yloxy)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl)-acetamide
  参考文献：
  名称：

  Structure–activity relationship in the oxazolidinone–quinolone hybrid series: influence of the central spacer on the antibacterial activity and the mode of action

  摘要：

  Oxazolidinone-quinolone hybrids, which combine the pharmacophores of a quinolone and an oxazolidinone, were synthesised and shown to be active against a variety of susceptible and resistant Gram-positive and Gram-negative bacteria. The nature of the spacer greatly influences the antibacterial activity by directing the mode of action, that is quinotone- and/or oxazolidinone-like activity. The best compounds in this series have a balanced dual mode of action and overcome all types of resistance, including resistance to quinolones and linezolid, in clinically relevant Gram-positive pathogens. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.028

文献信息

• USE OF OXAZOLIDINONE-QUINOLINE HYBRID ANTIBIOTICS FOR THE TREATMENT OF ANTHRAX AND OTHER INFECTIONS
  申请人：Hubschwerlen Christian

  公开号：US20120322766A1

  公开（公告）日：2012-12-20

  The present invention relates to the use of compounds, in which the pharmacophores of quinolone and oxazolidinone are chemically linked together through a linker that is stable under physiological conditions, for the treatment of anthrax and other infections.

  本发明涉及使用化合物，其中喹诺酮和噁唑烷酮的药效团经过稳定在生理条件下的连接剂化学连接在一起，用于治疗炭疽和其他感染病。
• [EN] USE OF OXAZOLIDINONE-QUINOLINE HYBRID ANTIBIOTICS FOR THE TREATMENT OF ANTHRAX AND OTHER INFECTIONS<br/>[FR] UTILISATION D'ANTIBIOTIQUES HYBRIDES D'OXAZOLIDINONE-QUINOLEINE DESTINES AU TRAITEMENT DE L'ANTHRAX ET D'AUTRES INFECTIONS
  申请人：MORPHOCHEM AG KOMB CHEMIE

  公开号：WO2004096221A1

  公开（公告）日：2004-11-11

  The present invention relates to the use of compounds, in which the pharmacophores of quinolone and oxazolidinone are chemically linked together through a linker that is stable under physiological conditions, for the treatment of anthrax and other infections.

  本发明涉及使用化合物，其中喹诺酮和噁唑烷酮的药效团通过在生理条件下稳定的连接剂化学连接在一起，用于治疗炭疽和其他感染。
• Intermediate products for producing oxazolidinone-quinolone hybrids
  申请人：Hubschwerlen Christian

  公开号：US20070004769A1

  公开（公告）日：2007-01-04

  The present invention describes intermediates (ZP) for a novel and efficient synthesis of compounds in which the pharmacophores of quinolone and oxazolidinone are linked to one another by way of a chemically stable linker.

  本发明描述了一种中间体（ZP），用于一种新颖有效的化合物合成方法，其中喹诺酮和噁唑烷酮的药效团通过化学稳定的连接剂相互连接。
• Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections
  申请人：Hubschwerlen Christian

  公开号：US20070155714A1

  公开（公告）日：2007-07-05

  The present invention relates to the use of compounds, in which the pharmacophores of quinolone and oxazolidinone are chemically linked together through a linker that is stable under physiological conditions, for the treatment of anthrax and other infections.

  本发明涉及使用化合物，其中喹诺酮和噁唑烷酮的药效团通过在生理条件下稳定的链接剂进行化学连接，用于治疗炭疽病和其他感染。
• US7557214B2
  申请人：——

  公开号：US7557214B2

  公开（公告）日：2009-07-07