N-{(S)-3-[3-Fluoro-4-((R)-1-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide | 790703-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-{(S)-3-[3-Fluoro-4-((R)-1-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide
• CAS: 790703-05-8
• 化学式: C₁₇H₂₂FN₃O₄
• 分子量: 351.378
• InChiKey: XZDNNJOEOJKBCL-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  79.9
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  环丙基萘啶羧酸 、 N-{(S)-3-[3-Fluoro-4-((R)-1-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-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-[(3R)-3-[[4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenoxy]methyl]pyrrolidin-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：

  R-1-CBZ-3-哌啶甲醇 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-{(S)-3-[3-Fluoro-4-((R)-1-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-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