(S) 2-[(3-mercapto-propionyl)-methyl-amino]-3-phenyl-propanoic acid | 80900-77-2

• 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) 2-[(3-mercapto-propionyl)-methyl-amino]-3-phenyl-propanoic acid
• 英文别名: (2S)-2-[methyl(3-sulfanylpropanoyl)amino]-3-phenylpropanoic acid
• CAS: 80900-77-2
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: NCQWMIDMMZIYGM-NSHDSACASA-N

物化性质

• 沸点：
  457.9±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-L-苯丙氨酸 在 ammonium hydroxide 、 sodium hydroxide 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 5.5h， 生成 (S) 2-[(3-mercapto-propionyl)-methyl-amino]-3-phenyl-propanoic 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

• New effector conjugates, process for their production and their pharmaceutical use
  申请人：Berger Markus

  公开号：US20050026971A1

  公开（公告）日：2005-02-03

  Conjugates of epothilones and epothilone derivatives (as effectors) with suitable biomolecules (as recognition units) are described. Their production is carried out by the effectors being reacted with suitable linkers, and the compounds that are produced are conjugated to the recognition units. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.

  本文介绍了依普托利酮及其衍生物（作为效应物）与适当的生物分子（作为识别单元）的共轭体。它们的制备是通过将效应物与适当的连接剂反应，然后将产生的化合物与识别单元结合而实现的。本文还介绍了这些共轭体在治疗增殖或血管生成相关过程中的药物应用。
• NEW EFFECTOR CONJUGATES, PROCESS FOR THEIR PRODUCTION AND THEIR PHARMACEUTICAL USE
  申请人：Schering AG

  公开号：EP1524979A2

  公开（公告）日：2005-04-27
• US7129254B2
  申请人：——

  公开号：US7129254B2

  公开（公告）日：2006-10-31
• US7335775B2
  申请人：——

  公开号：US7335775B2

  公开（公告）日：2008-02-26
• [EN] NEW EFFECTOR CONJUGATES, PROCESS FOR THEIR PRODUCTION AND THEIR PHARMACEUTICAL USE<br/>[FR] NOUVEAUX CONJUGUES D'EFFECTEURS, PROCEDES PERMETTANT DE LES PRODUIRE ET UTILISATION PHARMACEUTIQUE DE CEUX-CI
  申请人：SCHERING AG

  公开号：WO2004012735A2

  公开（公告）日：2004-02-12

  Conjugates of epothilones and epothilone derivatives (as effectors) with suitable biomolecules (as recognition units) are described. Their production is carried out by the effectors being reacted with suitable linkers, and the compounds that are produced are conjugated to the recognition units. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.