1-(2-hydroxyethyl)-4-(4-methylthiophenyl)-3-phenylpyrazol-5-ol | 691881-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-hydroxyethyl)-4-(4-methylthiophenyl)-3-phenylpyrazol-5-ol
• CAS: 691881-09-1
• 化学式: C₁₈H₁₈N₂O₂S
• 分子量: 326.419
• InChiKey: BWWBHXFPYNQHPY-UHFFFAOYSA-N

物化性质

• 熔点：
  235-237 °C
• 沸点：
  511.6±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.28
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyethyl)-4-(4-methylthiophenyl)-3-phenylpyrazol-5-ol 在 Oxone 、 polymer supported triphenylphosphine 、 四溴化碳 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 7-(4-Methylsulfonylphenyl)-6-phenyl-2,3-dihydropyrazolo[5,1-b][1,3]oxazole
  参考文献：
  名称：

  Synthesis and selective cyclooxygenase-2 (COX-2) inhibitory activity of a series of novel bicyclic pyrazoles

  摘要：

  Novel series of pyrazolo[5, 1-b] 1,3-oxazolidines, pyrazolo[5, 1-b] 1,3-oxazines and imidazolidino[1,2-d]pyrazoles were synthesized. These compounds were evaluated in vitro for their ability to inhibit cyclo oxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) in human whole blood (HWB). Several of the compounds were found to be novel and selective COX-2 inhibitors, the most potent and selective being 1-(5-cyclohexyl (2H, 3 H -pyrazolo [5, 1-b]-1, 3-oxazolidin-6-yl)-4-(methylsulfonyl)benzene, 7a (IC50 for COX-1 > 100 muM; for COX-2 = 1.3 M). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.012
• 作为产物：
  描述：

  4-甲硫基苯乙酸 在 硫酸 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 35.17h， 生成 1-(2-hydroxyethyl)-4-(4-methylthiophenyl)-3-phenylpyrazol-5-ol
  参考文献：
  名称：

  Synthesis and selective cyclooxygenase-2 (COX-2) inhibitory activity of a series of novel bicyclic pyrazoles

  摘要：

  Novel series of pyrazolo[5, 1-b] 1,3-oxazolidines, pyrazolo[5, 1-b] 1,3-oxazines and imidazolidino[1,2-d]pyrazoles were synthesized. These compounds were evaluated in vitro for their ability to inhibit cyclo oxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) in human whole blood (HWB). Several of the compounds were found to be novel and selective COX-2 inhibitors, the most potent and selective being 1-(5-cyclohexyl (2H, 3 H -pyrazolo [5, 1-b]-1, 3-oxazolidin-6-yl)-4-(methylsulfonyl)benzene, 7a (IC50 for COX-1 > 100 muM; for COX-2 = 1.3 M). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.012