ethyl 2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)ethanoate | 67909-77-7

• 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: ethyl 2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)ethanoate
• 英文别名: (2-oxo-4,5-diphenyl-oxazol-3-yl)-acetic acid ethyl ester；Ethyl 2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)acetate
• CAS: 67909-77-7
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: BBMKTUFGFMSYSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)ethanoate 在 氢氧化钾 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以85%的产率得到3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one
  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
• 作为产物：
  描述：

  4,5-diphenyloxazol-2-one 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以85%的产率得到ethyl 2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)ethanoate
  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

文献信息

• Ninomiya,I. et al., Heterocycles, 1978, vol. 9, p. 853 - 857
  作者：Ninomiya,I. et al.

  DOI：——

  日期：——
• Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors
  作者：Yasemin Dündar、Serdar Ünlü、Erden Banoğlu、Antonio Entrena、Gabriele Costantino、Maria-Teresa Nunez、Francisco Ledo、M. Fethi Şahin、Ningur Noyanalpan

  DOI：10.1016/j.ejmech.2008.10.039

  日期：2009.5

  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.