2-(4-Bromo-phenyl)-4-[1-ethoxy-prop-(Z)-ylidene]-4H-oxazol-5-one | 699012-69-6

• 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-prop-(Z)-ylidene]-4H-oxazol-5-one
• CAS: 699012-69-6
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: XMNCGSDOHGDOJO-QXMHVHEDSA-N

物化性质

• 沸点：
  374.2±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-prop-(Z)-ylidene]-4H-oxazol-5-one 、 (S)-Azetidine-2-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 (S)-1-{1-[2-(4-Bromo-phenyl)-5-oxo-oxazol-(4Z)-ylidene]-propyl}-azetidine-2-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-prop-(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