5,5-diphenyl-3-((4-phenylpiperazin-1-yl)methyl)imidazolidine-2,4-dione | 21598-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5,5-diphenyl-3-((4-phenylpiperazin-1-yl)methyl)imidazolidine-2,4-dione
• 英文别名: 5,5-diphenyl-3-(4-phenyl-piperazin-1-ylmethyl)-imidazolidine-2,4-dione；Hydantoin, 5,5-diphenyl-3-((4-phenylpiperazinyl)methyl)-；5,5-diphenyl-3-[(4-phenylpiperazin-1-yl)methyl]imidazolidine-2,4-dione
• CAS: 21598-65-2
• 化学式: C₂₆H₂₆N₄O₂
• 分子量: 426.518
• InChiKey: JPGUNGBAVAPKTA-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 N-苯基哌嗪 、 苯妥英 以 乙醇 为溶剂， 以74%的产率得到5,5-diphenyl-3-((4-phenylpiperazin-1-yl)methyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of novel N-Mannich bases derived from 5,5-diphenyl and 5,5-di(propan-2-yl)imidazolidine-2,4-dione core

  摘要：

  The aim of this study was to design and synthesize two series of N-Mannich bases with imidazolidine-2,4-dione core as a potential anticonvulsant with reduced toxicity and broad antiseizure activity. Preliminary screening revealed that the majority of synthesized compounds were effective in the maximal electroshock seizure (MES) and/or subcutaneous pentylenetetrazole (scPTZ) test. The most active in vivo compound, 18 (3-((4-methylpiperazin-1-yl)methyl)-5,5-diphenylimidazolidine-2,4-dione), exhibited an ED50 value comparable to that of phenytoin in the MES test (38.5 mg/kg vs 28.1 mg/kg), and more importantly, it showed four times higher potency than phenytoin in the 6 Hz test (12.2 mg/kg vs > 60 mg/kg). Additionally, 18 exhibited antiallodynic properties in the von Frey test in neuropathic (oxaliplatin-treated) mice. Compound 18 also demonstrated a broader spectrum of anticonvulsant activity than phenytoin and showed statistically significant antinociceptive properties in selected models of chronic pain.

  DOI：

  10.1016/j.bmcl.2019.06.001

文献信息

• Synthesis and pharmacological evaluation of novel N-Mannich bases derived from 5,5-diphenyl and 5,5-di(propan-2-yl)imidazolidine-2,4-dione core
  作者：Anna Czopek、Hanna Byrtus、Agnieszka Zagórska、Joanna Rychtyk、Małgorzata Góra、Kinga Sałat、Anna Rapacz、Jolanta Obniska

  DOI：10.1016/j.bmcl.2019.06.001

  日期：2019.8

  The aim of this study was to design and synthesize two series of N-Mannich bases with imidazolidine-2,4-dione core as a potential anticonvulsant with reduced toxicity and broad antiseizure activity. Preliminary screening revealed that the majority of synthesized compounds were effective in the maximal electroshock seizure (MES) and/or subcutaneous pentylenetetrazole (scPTZ) test. The most active in vivo compound, 18 (3-((4-methylpiperazin-1-yl)methyl)-5,5-diphenylimidazolidine-2,4-dione), exhibited an ED50 value comparable to that of phenytoin in the MES test (38.5 mg/kg vs 28.1 mg/kg), and more importantly, it showed four times higher potency than phenytoin in the 6 Hz test (12.2 mg/kg vs > 60 mg/kg). Additionally, 18 exhibited antiallodynic properties in the von Frey test in neuropathic (oxaliplatin-treated) mice. Compound 18 also demonstrated a broader spectrum of anticonvulsant activity than phenytoin and showed statistically significant antinociceptive properties in selected models of chronic pain.