3-[(hydroxyacetamido)methyl]-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-one | 525602-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[(hydroxyacetamido)methyl]-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-one
• CAS: 525602-01-1
• 化学式: C₁₆H₂₁N₃O₃
• 分子量: 303.361
• InChiKey: AUVYTJIASLFHQK-UHFFFAOYSA-N

物化性质

• 密度：
  1.211±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.26
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  naproxen chloride 、 3-[(hydroxyacetamido)methyl]-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-one 以 二氯甲烷 为溶剂， 反应 1.0h， 以1.8 g的产率得到naproxen-hydroxyacetamidopropyphenazone
  参考文献：
  名称：

  Biological and metabolic study of naproxen–propyphenazone mutual prodrug

  摘要：

  Naproxen-propyphenazone (NAP-PP) esters were synthesized as prodrugs with the aim of improving the therapeutic index through prevention of gastrointestinal irritation and bleeding. The structures of the synthesized NAP-PP hybrid esters were confirmed by IR and H-1 NMR spectroscopy and their purity was established by elemental analysis, HPLC and TLC. The release of NAP as well as PP derivatives. from the ester prodrugs was studied. A validated analytical HPLC method for the estimation of the NAP, and the prodrugs was developed, Also the enzymatic hydrolysis products of the ester were identified by GC-MS and in conjugation with HPLC. The kinetics of ester hydrolysis was studied in two different non-enzymatic buffer solutions, at pH 1.2, and 7.4 as well as in liver homogenates. Study of analgesic and anti-inflammatory properties in comparison with the reference compounds has shown that both analgesic and anti-inflammatory activities were present at the same doses of the investigated compounds, The ester III was found to be less irritating to gastric mucosal membrane than the parent drugs. These results suggest that the synthesized prodrugs are characterized by better therapeutic index than the parent drugs. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00159-8
• 作为产物：
  描述：

  5-(bromomethyl)-4-isopropyl-1-methyl-2-phenyl-1H-pyrazol-3(2H)-one 在 盐酸 、 乌洛托品 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-[(hydroxyacetamido)methyl]-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-one
  参考文献：
  名称：

  Biological and metabolic study of naproxen–propyphenazone mutual prodrug

  摘要：

  Naproxen-propyphenazone (NAP-PP) esters were synthesized as prodrugs with the aim of improving the therapeutic index through prevention of gastrointestinal irritation and bleeding. The structures of the synthesized NAP-PP hybrid esters were confirmed by IR and H-1 NMR spectroscopy and their purity was established by elemental analysis, HPLC and TLC. The release of NAP as well as PP derivatives. from the ester prodrugs was studied. A validated analytical HPLC method for the estimation of the NAP, and the prodrugs was developed, Also the enzymatic hydrolysis products of the ester were identified by GC-MS and in conjugation with HPLC. The kinetics of ester hydrolysis was studied in two different non-enzymatic buffer solutions, at pH 1.2, and 7.4 as well as in liver homogenates. Study of analgesic and anti-inflammatory properties in comparison with the reference compounds has shown that both analgesic and anti-inflammatory activities were present at the same doses of the investigated compounds, The ester III was found to be less irritating to gastric mucosal membrane than the parent drugs. These results suggest that the synthesized prodrugs are characterized by better therapeutic index than the parent drugs. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00159-8