4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonyl chloride | 1155180-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonyl chloride
• 英文别名: 4-(3-Methyl-2-oxo-4-phenyl-1,3-oxazol-5-yl)benzenesulfonyl chloride
• CAS: 1155180-52-1
• 化学式: C₁₆H₁₂ClNO₄S
• 分子量: 349.795
• InChiKey: SFDZOUCMRGYDHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonyl chloride 在 ammonium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 以45%的产率得到4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonamide
  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：

  3-Methyl-4,5-diphenyl-4-oxazolin-2-one 在 氯磺酸 作用下， 以66%的产率得到4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonyl chloride
  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