(RS)-3-(2,4,5-trimethoxyphenyl)-2-methylalanine | 75014-03-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (RS)-3-(2,4,5-trimethoxyphenyl)-2-methylalanine
• 英文别名: 2-amino-2-methyl-3-(2,4,5-trimethoxyphenyl)propanoic acid
• CAS: 75014-03-8
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: LCRAQGFNPHVTRN-UHFFFAOYSA-N

物化性质

• 沸点：
  415.5±45.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  91.01
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (RS)-3-(2,4,5-trimethoxyphenyl)-2-methylalanine 在 盐酸 、 sodium hydroxide 、 3 A molecular sieve 、 50W-X₈ ion exchange resin (H+ form) 、 氢溴酸 、 溶剂黄146 作用下， 反应 15.0h， 生成 (R)-6-OH-α-Me-Dopa
  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：

  (RS)-5-methyl-5-(2,4,5-trimethoxyphenyl)hydantoin 在 barium carbonate 作用下， 以 水 为溶剂， 反应 48.0h， 以67%的产率得到(RS)-3-(2,4,5-trimethoxyphenyl)-2-methylalanine
  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

文献信息

• Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine
  作者：D. G. Musson、D. Karashima、H. Rubiero、K. L. Melmon、A. Cheng、N. Castagnoli

  DOI：10.1021/jm00186a007

  日期：1980.12

  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.