1,1-dimethylethyl α-<((R,S)-acetylthio)methyl>benzenebutanoate | 156757-40-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,1-dimethylethyl α-<((R,S)-acetylthio)methyl>benzenebutanoate
• 英文别名: Tert-butyl 2-(acetylsulfanylmethyl)-4-phenylbutanoate
• CAS: 156757-40-3
• 化学式: C₁₇H₂₄O₃S
• 分子量: 308.442
• InChiKey: JODTXBPVJSJVDR-UHFFFAOYSA-N

物化性质

• 沸点：
  410.9±45.0 °C(predicted)
• 密度：
  1.079±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl α-<((R,S)-acetylthio)methyl>benzenebutanoate 在 三氟乙酸 作用下， 反应 0.5h， 以52%的产率得到α-<((R,S)-acetylthio)methyl>benzenebutanoic 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-dimethylethyl 2-(2-phenylethyl)-3-oxobutanoate 在 正丁基锂 、 二异丙胺 作用下， 反应 74.17h， 生成 1,1-dimethylethyl α-<((R,S)-acetylthio)methyl>benzenebutanoate
  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.