2-(4-Bromo-phenyl)-4-[1-ethoxy-meth-(Z)-ylidene]-4H-oxazol-5-one | 748184-90-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(4-Bromo-phenyl)-4-[1-ethoxy-meth-(Z)-ylidene]-4H-oxazol-5-one
• CAS: 748184-90-9
• 化学式: C₁₂H₁₀BrNO₃
• 分子量: 296.12
• InChiKey: MAGGGTMWTXSXFO-YFHOEESVSA-N

物化性质

• 沸点：
  351.2±52.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-Bromo-phenyl)-4-[1-ethoxy-meth-(Z)-ylidene]-4H-oxazol-5-one 、 Piperidine-3-carboxylic acid [(S)-1-carbamoyl-2-(4-hydroxy-phenyl)-ethyl]-amide 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 1-[2-(4-Bromo-phenyl)-5-oxo-oxazol-(4Z)-ylidenemethyl]-piperidine-3-carboxylic acid [(S)-1-carbamoyl-2-(4-hydroxy-phenyl)-ethyl]-amide
  参考文献：
  名称：

  Potent and selective inhibitors of bacterial methionyl tRNA synthetase derived from an oxazolone–dipeptide scaffold

  摘要：

  The preparation and structure-activity relationships (SARs) of potent and selective small molecule inhibitors of bacterial methionyl-tRNA synthetase (MetRS) derived from an oxazolone-dipeptide scaffold are described. Examples combine Staphylococcus aureus MetRS (SaMetRS) potency with selectivity over human MetRS. As a result of the SAR expansion compound 14a was identified, as a potent SaMetRS inhibitor (IC50 = 18 nM) having moderate inhibition of MetRS derived from Enterococci faecalis (IC50 = 3.51 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.094
• 作为产物：
  描述：

  4-溴苯甲酰氯 在 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-Bromo-phenyl)-4-[1-ethoxy-meth-(Z)-ylidene]-4H-oxazol-5-one
  参考文献：
  名称：

  Potent and selective inhibitors of bacterial methionyl tRNA synthetase derived from an oxazolone–dipeptide scaffold

  摘要：

  The preparation and structure-activity relationships (SARs) of potent and selective small molecule inhibitors of bacterial methionyl-tRNA synthetase (MetRS) derived from an oxazolone-dipeptide scaffold are described. Examples combine Staphylococcus aureus MetRS (SaMetRS) potency with selectivity over human MetRS. As a result of the SAR expansion compound 14a was identified, as a potent SaMetRS inhibitor (IC50 = 18 nM) having moderate inhibition of MetRS derived from Enterococci faecalis (IC50 = 3.51 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.094