S-(2S,3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-2-(hydroxycarbamoyl)-5-methylhexyl ethanethioate | 130370-62-6

• 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-(2S,3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-2-(hydroxycarbamoyl)-5-methylhexyl ethanethioate
• 英文别名: S-[(2S,3R)-2-(hydroxycarbamoyl)-5-methyl-3-[[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]hexyl] ethanethioate
• CAS: 130370-62-6
• 化学式: C₂₁H₃₁N₃O₅S
• 分子量: 437.56
• InChiKey: OYQBDHGRUGQQAP-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-(2S,3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-2-(hydroxycarbamoyl)-5-methylhexyl ethanethioate 在 sodium methylate 作用下， 以97%的产率得到(2R,3S)-N⁴-Hydroxy-2-isobutyl-3-mercaptomethyl-N¹-((S)-1-methylcarbamoyl-2-phenyl-ethyl)-succinamide
  参考文献：
  名称：

  Synthesis of an Inhibitor-Tethered Resin for Detection of Active Matrix Metalloproteinases Involved in Disease

  摘要：

  Matrix metalloproteinases ( MMPs), of which 26 members are known in humans, are implicated in a number of diseases. Their activity is strictly controlled, but when the biological control over the activity is lost, disease processes set in. In an attempt to delineate what MMP activity has gone awry in what diseases, including metastatic cancers that are of special interest to our laboratories, we conceived and synthesized two chromatographic resins incorporated with a multifunctional broad- spectrum inhibitor for MMPs. The broad-spectrum inhibitor contains three sterogentic centers and was synthesized in 13 steps. Two structural variants of the inhibitors were linked to the polymer support via disulfide moieties. These resins are intended for use in cellular systems to selectively fish out from a complex mixture of all cellular proteins the active MMP forms important for the specific disease for identification.

  DOI：

  10.1021/jo060058h
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 在 羟胺 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 S-(2S,3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-2-(hydroxycarbamoyl)-5-methylhexyl ethanethioate
  参考文献：
  名称：

  Synthesis of an Inhibitor-Tethered Resin for Detection of Active Matrix Metalloproteinases Involved in Disease

  摘要：

  Matrix metalloproteinases ( MMPs), of which 26 members are known in humans, are implicated in a number of diseases. Their activity is strictly controlled, but when the biological control over the activity is lost, disease processes set in. In an attempt to delineate what MMP activity has gone awry in what diseases, including metastatic cancers that are of special interest to our laboratories, we conceived and synthesized two chromatographic resins incorporated with a multifunctional broad- spectrum inhibitor for MMPs. The broad-spectrum inhibitor contains three sterogentic centers and was synthesized in 13 steps. Two structural variants of the inhibitors were linked to the polymer support via disulfide moieties. These resins are intended for use in cellular systems to selectively fish out from a complex mixture of all cellular proteins the active MMP forms important for the specific disease for identification.

  DOI：

  10.1021/jo060058h