(2R)-2-[[(2R)-2-(acetylsulfanylmethyl)-3-(4-phenylphenyl)propanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoic acid | 115370-06-4

• 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: (2R)-2-[[(2R)-2-(acetylsulfanylmethyl)-3-(4-phenylphenyl)propanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoic acid
• CAS: 115370-06-4
• 化学式: C₂₉H₃₁NO₄S₂
• 分子量: 521.701
• InChiKey: NWAZXECIIWNDNC-SVBPBHIXSA-N

物化性质

• 沸点：
  758.1±60.0 °C(predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[(2R)-2-(acetylsulfanylmethyl)-3-(4-phenylphenyl)propanoyl]amino]-3-[(4-methylphenyl)methylsulfanyl]propanoic acid 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以27%的产率得到(2R)-3-[(4-methylphenyl)methylsulfanyl]-2-[[(2R)-2-[(4-phenylphenyl)methyl]-3-sulfanylpropanoyl]amino]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：

  [(1,1'-联苯基)-4-基甲基]丙二酸 在 盐酸 、 氯化亚砜 、 二甲胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 93.0h， 生成 (2R)-2-[[(2R)-2-(acetylsulfanylmethyl)-3-(4-phenylphenyl)propanoyl]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

文献信息

• Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S-alkylcysteine derivatives
  作者：Bernard R. Neustadt、Elizabeth M. Smith、Terry L. Nechuta、Alan A. Bronnenkant、Martin F. Haslanger、Robert W. Watkins、Caroline J. Foster、Edmund J. Sybertz

  DOI：10.1021/jm00041a026

  日期：1994.7

  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.