(R)-tert-butyl 3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoate | 908350-11-8

• 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: (R)-tert-butyl 3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoate
• 英文别名: tert-butyl (3R)-5-methyl-3-[[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]-2-methylidenehexanoate
• CAS: 908350-11-8
• 化学式: C₂₃H₃₄N₂O₄
• 分子量: 402.534
• InChiKey: XLABNPYNIAAVQZ-MOPGFXCFSA-N

物化性质

• 沸点：
  611.4±55.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoate 在 N-甲基吗啉 、 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 乙胺嗪 、 丹酰尸胺 、 盐酸羟胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R)-N-hydroxy-N'-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(phenacylsulfanylmethyl)butanediamide
  参考文献：
  名称：

  Selective inhibition of low affinity IgE receptor (CD23) processing

  摘要：

  A series of hydroxamic acids related to the non-selective matrix metalloproteinase inhibitor Batimastat has been prepared, some members of which are potent inhibitors of the processing of the low affinity IgE receptor (CD 23). Increased activity is obtained by appropriate substitution at the a-position, whilst selectivity is gained by use of a P1' benzyl group in conjunction with a C-terminal primary amide. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10149-4
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 在 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 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (R)-tert-butyl 3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoate
  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

文献信息

• Synthesis of an Inhibitor-Tethered Resin for Detection of Active Matrix Metalloproteinases Involved in Disease
  作者：Dusan Hesek、Marta Toth、Viktor Krchňák、Rafael Fridman、Shahriar Mobashery

  DOI：10.1021/jo060058h

  日期：2006.8.1

  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.
• Selective inhibition of low affinity IgE receptor (CD23) processing
  作者：Stuart Bailey、Brian Bolognese、Derek R Buckle、Andrew Faller、Sally Jackson、Pearl Louis-Flamberg、Mark McCord、Ruth J Mayer、Lisa A Marshall、David G Smith

  DOI：10.1016/s0960-894x(97)10149-4

  日期：1998.1

  A series of hydroxamic acids related to the non-selective matrix metalloproteinase inhibitor Batimastat has been prepared, some members of which are potent inhibitors of the processing of the low affinity IgE receptor (CD 23). Increased activity is obtained by appropriate substitution at the a-position, whilst selectivity is gained by use of a P1' benzyl group in conjunction with a C-terminal primary amide. (C) 1997 Elsevier Science Ltd. All rights reserved.