1-Pyrrolidinecarboxylic acid,3-[2-[2-fluoro-4-[[(phenylmethoxy)carbonyl]amino]phenoxy]ethyl]-,phenylmethyl ester | 648418-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Pyrrolidinecarboxylic acid,3-[2-[2-fluoro-4-[[(phenylmethoxy)carbonyl]amino]phenoxy]ethyl]-,phenylmethyl ester
• 英文别名: 3-[2-(4-Benzyloxycarbonylamino-2-fluoro-phenoxy)-ethyl]-pyrrolidine-1-carboxylic acid benzyl ester
• CAS: 648418-13-7
• 化学式: C₂₈H₂₉FN₂O₅
• 分子量: 492.547
• InChiKey: NGOSADHPJYUHBB-UHFFFAOYSA-N

物化性质

• 沸点：
  604.9±55.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-Pyrrolidinecarboxylic acid,3-[2-[2-fluoro-4-[[(phenylmethoxy)carbonyl]amino]phenoxy]ethyl]-,phenylmethyl ester 在 正丁基锂 、 sodium azide 、 TEA 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-{2-[4-((R)-5-Azidomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenoxy]-ethyl}-pyrrolidine-1-carboxylic acid benzyl ester
  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-[2-(2-Fluoro-4-nitro-phenoxy)-ethyl]-pyrrolidine-1-carboxylic acid benzyl ester 在 盐酸 、 碳酸氢钠 、 锌 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 1-Pyrrolidinecarboxylic acid,3-[2-[2-fluoro-4-[[(phenylmethoxy)carbonyl]amino]phenoxy]ethyl]-,phenylmethyl ester
  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