3-(4,4-diethoxyoxan-3-yl)oxy-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1H-pyrazole | 791806-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4,4-diethoxyoxan-3-yl)oxy-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1H-pyrazole
• CAS: 791806-41-2
• 化学式: C₂₅H₂₉FN₂O₆S
• 分子量: 504.579
• InChiKey: NDPVPWIOCBEVMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(4,4-diethoxyoxan-3-yl)oxy-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1H-pyrazole 在 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以100 mg的产率得到3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-7,8-dihydro-5H-pyrazolo[5,1-b]pyrano[4,3-d][1,3]oxazole
  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：

  对甲硫基苯甲腈 在 过氧乙酸 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 一水合肼 、 magnesium 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.5h， 生成 3-(4,4-diethoxyoxan-3-yl)oxy-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1H-pyrazole
  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