N-[3-phenyl-2-mercaptomethylpropionyl]-S-methionine | 88424-57-1

• 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: N-[3-phenyl-2-mercaptomethylpropionyl]-S-methionine
• 英文别名: N-[3-Mercapto-2(R,S)-Benzylpropionyl]-L-Methionine；(2S)-2-[(2-benzyl-3-sulfanylpropanoyl)amino]-4-methylsulfanylbutanoic acid
• CAS: 88424-57-1
• 化学式: C₁₅H₂₁NO₃S₂
• 分子量: 327.469
• InChiKey: HNZBQOSYCFLCAE-ABLWVSNPSA-N

物化性质

• 沸点：
  592.8±50.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[(乙酰巯基)甲基]-3-苯基丙酸 在 N-甲基吗啉 、 sodium hydroxide 、 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 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 N-[3-phenyl-2-mercaptomethylpropionyl]-S-methionine
  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

• Sulfur-containing acylamino acids. I. Syntheses and angiotensin I converting enzyme-inhibitory activities of sulfur-containing N-mercaptoalkanoyl amino acids.
  作者：TAKETOSHI KOMORI、KATSUMI ASANO、YASUTO SASAKI、HIROMI HANAI、RUMI SEO、MASANORI TAKAOKA、SHIRO MORIMOTO、MIKIO HORI

  DOI：10.1248/cpb.35.2382

  日期：——

  N-Mercaptoalkanoyl derivatives of sulfur-containing amino acids were synthesized and examined for inhibitory effects on angiotensin I converting enzyme (ACE) extracted from rabbit lung. Inhibition of ACE was determined by means of a spectrometric assay with hippuryl-L-histidyl-L-leucine as a substrate. Among the synthesized sulfur-containing compounds, N- (2-benzyl-3-mercaptopropanoyl) -S-methyl-L-cysteine (13a) and N- (2-benzyl-3-mercaptopropanoyl) -S-ethyl-L-cysteine (13c) showed the most potent inhibitory effects on ACE activity. The IC50 values of 13a and 13c on ACE activity were 0.028 and 0.020 μM, respectively.

  含硫氨基酸的N-巯基烷酰基衍生物被合成并检验了它们对从兔肺提取的血管紧张素I转化酶（ACE）的抑制作用。ACE的抑制作用是通过采用高脯酰-L-组氨酰-L-亮氨酸作为底物的光谱测定法确定的。在合成的含硫化合物中，N-(2-苄基-3-巯基丙酰基)-S-甲基-L-半胱氨酸（13a）和N-(2-苄基-3-巯基丙酰基)-S-乙基-L-半胱氨酸（13c）对ACE活性显示了最强大的抑制作用。13a和13c对ACE活性的IC50值分别为0.028和0.020 μM。
• Mercapto-acylamino acid antihypertensives
  申请人：Schering Corporation

  公开号：US04929641A1

  公开（公告）日：1990-05-29

  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.

  本发明揭示了在治疗高血压方面有用的新型巯基-酰基氨基酸，以及用于治疗高血压的巯基-酰基氨基酸和心房利钠肽因子或血管紧张素转换酶抑制剂的组合。
• Acylamino acid antihypertensives in the treatment of congestive heart
  申请人：Schering Corporation

  公开号：US05262436A1

  公开（公告）日：1993-11-16

  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.

  本发明揭示了用于治疗高血压的巯基-酰胺基酸以及巯基-酰胺基酸和心房利钠肽因子或血管紧张素转化酶抑制剂的组合物。
• Enkephalinase enzyme inhibiting compounds
  申请人：PFIZER INC.

  公开号：EP0066956A1

  公开（公告）日：1982-12-15

  Chiral 2-(2-benzyl-3-mercaptopropionylamino)-1-alkanol derivatives and chiral 2-(2-benzyl-3-mercaptopropionyl- amino)-4-methylthiobutyric acids are inhibitors of enkephalinase enzyme, reflecting their clinical utility as analgesics or anticonvulsant agents, or as therapy for disorders in which endogenous enkephalin levels are below normal.

  手性 2-(2-苄基-3-巯丙基氨基)-1-烷醇衍生物和手性 2-(2-苄基-3-巯丙基氨基)-4-甲硫基丁酸是脑啡肽酶的抑制剂，反映了它们作为镇痛剂或抗惊厥剂或治疗内源性脑啡肽水平低于正常的疾病的临床用途。
• Neutral metalloendopeptidase inhibitors in the treatment of hypertension
  申请人：SCHERING CORPORATION

  公开号：EP0254032A2

  公开（公告）日：1988-01-27

  The method of treating hypertension with neutral metalloendopeptidase (NMEP) inhibitors, NMEP inhibitors in combination with atrial peptides, and NMEP inhibitors in combination with angiotensin converting enzyme inhibitors, as well as pharmaceutical compositions therefor, are disclosed.

  本研究公开了使用中性金属内肽酶（NMEP）抑制剂、NMEP 抑制剂与心房肽联合使用、NMEP 抑制剂与血管紧张素转换酶抑制剂联合使用治疗高血压的方法及其药物组合物。