methyl (2R)-2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoate | 115370-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R)-2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoate
• CAS: 115370-11-1
• 化学式: C₂₄H₂₉NO₄S₂
• 分子量: 459.631
• InChiKey: PSXGKPRDQJGYGE-YADHBBJMSA-N

物化性质

• 沸点：
  646.6±55.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以78%的产率得到(2R)-2-[[(2S)-2-benzyl-3-sulfanylpropanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoic acid
  参考文献：
  名称：

  Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S-alkylcysteine derivatives

  摘要：

  A broad series of N-(3-mercaptoacyl) amino acid derivatives was evaluated for their ability to inhibit atriopeptidase (neutral endopeptidase, EC 3.4.24.11) in vitro and in vivo. Structural parameters studied were (i) the substituent on the 2-position of the 3-mercaptopropionyl moiety, (ii) the amino acid component, (iii) the S-terminal derivative, and (iv) the C-terminal derivative. Optimum activity was observed for derivatives of methionine and S-alkylcysteines. N-[3-Mercapto-2(S)-[(2-methylphenyl)methyl]-1-oxopropyl]-L-methionine was identified as a highly effective inhibitor of atriopeptidase meriting evaluation as a potential cardiovascular therapeutic agent.

  DOI：

  10.1021/jm00041a026
• 作为产物：
  描述：

  Boc-cysteine(4-Me-Bn) 在 N-甲基吗啉 、 氯化亚砜 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 methyl (2R)-2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoate
  参考文献：
  名称：

  Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S-alkylcysteine derivatives

  摘要：

  A broad series of N-(3-mercaptoacyl) amino acid derivatives was evaluated for their ability to inhibit atriopeptidase (neutral endopeptidase, EC 3.4.24.11) in vitro and in vivo. Structural parameters studied were (i) the substituent on the 2-position of the 3-mercaptopropionyl moiety, (ii) the amino acid component, (iii) the S-terminal derivative, and (iv) the C-terminal derivative. Optimum activity was observed for derivatives of methionine and S-alkylcysteines. N-[3-Mercapto-2(S)-[(2-methylphenyl)methyl]-1-oxopropyl]-L-methionine was identified as a highly effective inhibitor of atriopeptidase meriting evaluation as a potential cardiovascular therapeutic agent.

  DOI：

  10.1021/jm00041a026