1-[5-(4-Fluoro-phenyl)-4-(4-methylsulfanyl-phenyl)-1H-pyrazol-3-yloxy]-3,3-dimethyl-butan-2-one | 329076-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[5-(4-Fluoro-phenyl)-4-(4-methylsulfanyl-phenyl)-1H-pyrazol-3-yloxy]-3,3-dimethyl-butan-2-one
• 英文别名: 1-[[5-(4-fluorophenyl)-4-(4-methylsulfanylphenyl)-1H-pyrazol-3-yl]oxy]-3,3-dimethylbutan-2-one
• CAS: 329076-90-6
• 化学式: C₂₂H₂₃FN₂O₂S
• 分子量: 398.501
• InChiKey: OSWPBAWMEBFVQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[5-(4-Fluoro-phenyl)-4-(4-methylsulfanyl-phenyl)-1H-pyrazol-3-yloxy]-3,3-dimethyl-butan-2-one 在 过氧乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-[1-ethyl-5-(4-fluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-1H-pyrazol-3-yloxy]-3,3-dimethyl-butan-2-one
  参考文献：
  名称：

  Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors

  摘要：

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

  DOI：

  10.1021/jo049264k
• 作为产物：
  描述：

  ethyl 2-(4-methylthiophenyl)-2-(4-fluorobenzoyl)acetate 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-[5-(4-Fluoro-phenyl)-4-(4-methylsulfanyl-phenyl)-1H-pyrazol-3-yloxy]-3,3-dimethyl-butan-2-one
  参考文献：
  名称：

  Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors

  摘要：

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

  DOI：

  10.1021/jo049264k

文献信息

• US6472416B1
  申请人：——

  公开号：US6472416B1

  公开（公告）日：2002-10-29