2-<<2(S)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(methylthio)butanoyl>amino>ethanol | 156757-46-9

• 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: 2-<<2(S)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(methylthio)butanoyl>amino>ethanol
• 英文别名: tert-butyl N-[(2S)-1-(2-hydroxyethylamino)-4-methylsulfanyl-1-oxobutan-2-yl]carbamate
• CAS: 156757-46-9
• 化学式: C₁₂H₂₄N₂O₄S
• 分子量: 292.4
• InChiKey: NRQMVSDCHJCULS-VIFPVBQESA-N

物化性质

• 沸点：
  521.3±50.0 °C(predicted)
• 密度：
  1.138±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<<2(S)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(methylthio)butanoyl>amino>ethanol 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 N-<<2(S)-amino-4-(methylthio)butanoyl>amino>ethanol hydrochloride
  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-L-蛋氨酸 、 C.I.酸性橙108 在 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 5.0h， 以81%的产率得到2-<<2(S)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(methylthio)butanoyl>amino>ethanol
  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.