L-β-(3-mercapto-1-oxopropoxy)benzenepropanoic acid | 70506-40-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: L-β-(3-mercapto-1-oxopropoxy)benzenepropanoic acid
• 英文别名: (2S)-3-phenyl-2-(3-sulfanylpropanoyloxy)propanoic acid
• CAS: 70506-40-0
• 化学式: C₁₂H₁₄O₄S
• 分子量: 254.307
• InChiKey: OBWQYTZSBJXFIF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-(-)-3-苯基乳酸 在 ammonium hydroxide 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 反应 0.58h， 生成 L-β-(3-mercapto-1-oxopropoxy)benzenepropanoic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011

文献信息

• Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme
  作者：Michael E. Condon、Edward W. Petrillo、Denis E. Ryono、Joyce A. Reid、Richard Neubeck、Mohindar Puar、James E. Heikes、Emily F. Sabo、Kathryn A. Losee

  DOI：10.1021/jm00345a011

  日期：1982.3

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.