N-<3-(acetylthio)-2(R,S)-(phenylmethyl)-1-oxopropyl>-L-methionine methyl ester | 115406-21-8

• 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-(acetylthio)-2(R,S)-(phenylmethyl)-1-oxopropyl>-L-methionine methyl ester
• 英文别名: N-[3-Acetylthio-2(R,S)-Benzylpropionyl)-L-Methionine Methyl Ester；methyl (2S)-2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoate
• CAS: 115406-21-8
• 化学式: C₁₈H₂₅NO₄S₂
• 分子量: 383.533
• InChiKey: VFDSTIILDSXLCE-LYKKTTPLSA-N

物化性质

• 沸点：
  576.1±50.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-<3-(acetylthio)-2(R,S)-(phenylmethyl)-1-oxopropyl>-L-methionine methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到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
• 作为产物：
  描述：

  L-蛋氨酸甲酯盐酸盐 、 2-[(乙酰巯基)甲基]-3-苯基丙酸 在 N-甲基吗啉 、 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 20.0h， 以55%的产率得到N-<3-(acetylthio)-2(R,S)-(phenylmethyl)-1-oxopropyl>-L-methionine methyl ester
  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

• 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。
• US4329495A
  申请人：——

  公开号：US4329495A

  公开（公告）日：1982-05-11