(RS)-5-methyl-5-(2,4,5-trimethoxyphenyl)hydantoin | 75014-02-7

• 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: (RS)-5-methyl-5-(2,4,5-trimethoxyphenyl)hydantoin
• CAS: 75014-02-7
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: ZOMFTMDIOYEQGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  85.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (RS)-5-methyl-5-(2,4,5-trimethoxyphenyl)hydantoin 在 barium carbonate 作用下， 以 水 为溶剂， 反应 57.0h， 生成 2-甲基-3-(2,4,5-三羟基苯基)丙氨酸
  参考文献：
  名称：

  Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine

  摘要：

  The synthesis, resolution, and absolute configuration assignment of 2-methyl-3-(2,4,5-trihydroxphenyl)alanine (6-OH-alpha-Me-Dopa) are reported. Hemodynamic studies in the rat have shown that this structural analogue and potential metabolite of the clinically useful drug (S)-alpha-Me-Dopa possesses weak hypotensive activity which resides in the R enantiomer. LD50 studies in mice have established that 6-OH-alpha-Me-Dopa is over four times more toxic than alpha-Me-Dopa. Chronic exposure to 6-OH-alpha-Me-Dopa leads to renal and hepatic lesions. The case of oxidation of this hydroquinone to the electrophilic quinone species may contribute to its enhanced toxicity compared to alpha-Me-Dopa.

  DOI：

  10.1021/jm00186a007
• 作为产物：
  描述：

  1-(2,4,5-三甲氧基苯基)-2-硝基丙烯 在 碳酸氢铵 、 铁粉 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 9.5h， 生成 (RS)-5-methyl-5-(2,4,5-trimethoxyphenyl)hydantoin
  参考文献：
  名称：

  Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine

  摘要：

  The synthesis, resolution, and absolute configuration assignment of 2-methyl-3-(2,4,5-trihydroxphenyl)alanine (6-OH-alpha-Me-Dopa) are reported. Hemodynamic studies in the rat have shown that this structural analogue and potential metabolite of the clinically useful drug (S)-alpha-Me-Dopa possesses weak hypotensive activity which resides in the R enantiomer. LD50 studies in mice have established that 6-OH-alpha-Me-Dopa is over four times more toxic than alpha-Me-Dopa. Chronic exposure to 6-OH-alpha-Me-Dopa leads to renal and hepatic lesions. The case of oxidation of this hydroquinone to the electrophilic quinone species may contribute to its enhanced toxicity compared to alpha-Me-Dopa.

  DOI：

  10.1021/jm00186a007