4-(3-acetyl-5-phenyl-4-(phenylsulfonyl)-1H-pyrazol-1-yl)benzenesulfonamide | 1610556-07-4

• 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-(3-acetyl-5-phenyl-4-(phenylsulfonyl)-1H-pyrazol-1-yl)benzenesulfonamide
• 英文别名: 4-[3-Acetyl-4-(benzenesulfonyl)-5-phenylpyrazol-1-yl]benzenesulfonamide；4-[3-acetyl-4-(benzenesulfonyl)-5-phenylpyrazol-1-yl]benzenesulfonamide
• CAS: 1610556-07-4
• 化学式: C₂₃H₁₉N₃O₅S₂
• 分子量: 481.553
• InChiKey: HBZUALMGOGLJFP-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C
• 沸点：
  764.907±70.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.426±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  sodium benzenesulfonate 在 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 反应 15.33h， 生成 4-(3-acetyl-5-phenyl-4-(phenylsulfonyl)-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of N-benzenesulfonamide-1H-pyrazoles bearing arylsulfonyl moiety: Novel celecoxib analogs as potent anti-inflammatory agents

  摘要：

  The reaction of arylsulfones 11a-d with hydrazonoyl chloride derivative 13 furnished celecoxib analogs 4-(3-acetyl-5-aryl-4-(arylsulfonyl)-1H-pyrazol-1-yl)benzenesulfonamides 15a-d, respectively. Oximes 16a, b and hydrazones 17a, b were prepared by reacting sulfones 11a, b with hydroxyl amine and phenyl hydrazine, respectively. The anti-inflammatory activity of the synthesized compounds showed that, 5-(4-bromophenyl)-4-(phenylsulfonyl)pyrazole 15c and 5-(4-bromophenyl)-4-(4-tolylsulfonyl)pyrazole 15d exhibited excellent anti-inflammatory activity with ED50 = 68 ± 2.2 and 51 ± 0.7 μM/kg, respectively, higher than that of celecoxib (ED50 = 86 ± 1.1 μM/kg) after 3 h with acceptable ulcer index. In addition, the LD50 of 15c and 15d is 7.1 mM/kg for each, and 9.8 mM/kg for celecoxib. Compound 15d appeared selectivity index (COX-2/COX-1) almost the half of celecoxib while 15c is non-selective for COX-2. Compound 15c with ED50 = 80 ± 2.8 μM/kg showed a significant analgesic activity when compared with celecoxib (ED50 = 70 ± 3.9 μM/kg) after 2 h whereas 15b (ED50 = 50 ± 1.2 μM/kg) and 15d (ED50 = 69 ± 2.7 μM/kg) seemed to be more potent than celecoxib (ED50 = 156 ± 4.8 μM/kg) but with a shorter duration (0.5 h).

  DOI：

  10.1016/j.ejmech.2014.04.065