4-(4-phenyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonamide | 13342-74-0

• 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-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonamide
• 英文别名: 4-(2-oxo-4-phenyl-2,3-dihydro-oxazol-5-yl)-benzenesulfonamide；4-(2-oxo-4-phenyl-2,3-dihydro-1,3-oxazol-5-yl)benzenesulfonamide；4-Phenyl-5--oxazol-2-on；4-(2-oxo-4-phenyl-3H-1,3-oxazol-5-yl)benzenesulfonamide
• CAS: 13342-74-0
• 化学式: C₁₅H₁₂N₂O₄S
• 分子量: 316.337
• InChiKey: XQVSFQBKZWJYMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-phenyl-2-oxo-3H-1,3-oxazol-5-yl)benzenesulfonyl chloride 在 ammonium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以58%的产率得到4-(4-phenyl-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

文献信息

• 4-Aroylbenzils and related compounds
  作者：Hilton Greenberg、Theodorus Van Es、O. G. Backeberg

  DOI：10.1021/jo01285a006

  日期：1967.10
• COMBINATIONS COMPRISING AN HSP90 INHIBITOR AND A PHOPHODIESTERASE INHIBITOR FOR TREATING OR PREVENTING NEOPLASIA
  申请人：Pharmacia Corporation

  公开号：EP1682143A2

  公开（公告）日：2006-07-26
• [EN] COMBINATIONS COMPRISING AN Hsp90 INHIBITOR AND A PHOPHODIESTERASE INHIBITOR FOR TREATING OR PREVENTING NEOPLASIA<br/>[FR] ASSOCIATION DE L'INHIBITEUR DE HSP90 ET DE L'INHIBITEUR DE LA PHOPHODIESTERASE DESTINEE A TRAITER OU PREVENIR LA NEOPLASIE
  申请人：PHARMACIA CORP

  公开号：WO2005041879A2

  公开（公告）日：2005-05-12

  A method for treating or preventing neoplasia or a neoplasia-related disorder in a subject is provided, the method comprising administering to the subject an effective amount of a combination comprising an Hsp90 inhibitor and a phosphodiesterase inhibitor, and optionally a Cox-2 inhibitor.
• [EN] TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR<br/>[FR] TRAITEMENT OU PREVENTION DE LA NEOPLASIE A L'AIDE D'UN INHIBITEUR DE LA PROTEINE HSP90
  申请人：PHARMACIA CORP

  公开号：WO2005044194A2

  公开（公告）日：2005-05-19

  A method for treating or preventing neoplasia or a neoplasia-related disorder in a subject is provided, the method comprising administering to the subject an effective amount of an Hsp90 inhibitor, or of a combination comprising an Hsp90 inhibitor and a Cox-2 inhibitor.
• 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.