N-(2-phenylethyl)-2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)acetamide | 1155180-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-phenylethyl)-2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)acetamide
• 英文别名: 2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)-N-(2-phenylethyl)acetamide
• CAS: 1155180-71-4
• 化学式: C₂₅H₂₂N₂O₃
• 分子量: 398.461
• InChiKey: BOJQPIAXRHSBPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯乙胺 、 3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one 在 氯甲酸乙酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以56%的产率得到N-(2-phenylethyl)-2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors

  摘要：

  A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3H-1,3-oxazole derivatives were prepared as selective cyclooxygenase-2 (COX-2) inhibitors. Among the synthesized compounds, 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzensulfonamide (compound 6) showed selective COX-2 inhibition with a selectivity index of >50 (IC50COX-1 = >100 mu M, IC50COX-2 = 2 mu m) in purified enzyme (PE) assay. Compound 6 also exhibited selective COX-2 inhibition in human whole blood assay. Molecular docking studies showed that 6 can be docked into the COX-2 binding site thus providing the molecular basis for its activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.039