S-phenethyl-L-cysteine

• 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: S-phenethyl-L-cysteine
• 英文别名: (R)3-Mercapto-2-phenethylamino-propionic acid；(2R)-2-(2-phenylethylamino)-3-sulfanylpropanoic acid
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: TZUOMPROKVAFNT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-phenethyl-L-cysteine 在 氯化亚砜 作用下， 以 dichloromethane (CH2 Cl2) 、 乙醇 为溶剂， 生成 S-phenethyl-L-cysteine ethyl ester hydrochloride
  参考文献：
  名称：

  Mercapto-acylamino acid antihypertensives

  摘要：

  新型巯基-酰胺基酸在治疗高血压方面很有用，公开了巯基-酰胺基酸和心房利钠因子或抑制血管紧张素转化酶的组合物，用于治疗高血压。

  公开号：

  US05061710A1
• 作为产物：
  描述：

  L-半胱氨酸 、 苯乙醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 S-phenethyl-L-cysteine
  参考文献：
  名称：

  Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.

  DOI：

  10.1021/jm010272s

文献信息

• Mercapto-acylamino acid antihypertensives
  申请人：Schering Corporation

  公开号：US05061710A1

  公开（公告）日：1991-10-29

  Novel mercapto-acylamino acids useful in the treatment of hypertension and combinations of mercapto-acylamino acids and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for treating hypertension are disclosed.

  新型巯基-酰胺基酸在治疗高血压方面很有用，公开了巯基-酰胺基酸和心房利钠因子或抑制血管紧张素转化酶的组合物，用于治疗高血压。
• Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships
  作者：Jung Dae Park、Dong H. Kim

  DOI：10.1021/jm010272s

  日期：2002.2.1

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.