(R)-2-Amino-3-(3,4-dihydroxy-phenyl)-2-methyl-propionic acid ethyl ester | 1241679-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-Amino-3-(3,4-dihydroxy-phenyl)-2-methyl-propionic acid ethyl ester
• 英文别名: ethyl (2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate
• CAS: 1241679-32-2
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: SVEBYYWCXTVYCR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-3-(3,4-dihydroxy-phenyl)-2-methyl-propionic acid ethyl ester 在 phosphate buffer 、 phosphate buffer (PH = 7.4) 、 potassium hydrogencarbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 5.0h， 生成 (R)-5-Hydroxy-2-methyl-6-oxo-2,6-dihydro-1H-indole-2-carboxylic acid ethyl ester
  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.