benzyl (S)-5-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-6-((naphthalen-2-ylmethyl)amino)-6-oxohexanoate | 1200360-27-5

• 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: benzyl (S)-5-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-6-((naphthalen-2-ylmethyl)amino)-6-oxohexanoate
• CAS: 1200360-27-5
• 化学式: C₃₂H₃₉N₃O₆
• 分子量: 561.678
• InChiKey: MCTILKOWFNFSAS-CUNXSJBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-5-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-6-((naphthalen-2-ylmethyl)amino)-6-oxohexanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors

  摘要：

  A series of boron peptides 11, 13, 15 and 17 were designed and synthesized as proteasome inhibitors based on the structure of Belactosin C. Matteson homologation was a key step in the synthesis of the boron peptides. Compounds 11a and 13 showed significant inhibition of 20S proteasome chymotrypsin-like (beta 5) activity (IC(50) = 0.28 and 0.51 mu M, respectively). Furthermore, like PS-341, compound 11a increased the G2/M cell distribution. A biparametric cytofluorimetric analysis with FITC-labeled annexin V and propidium iodide showed induction of apoptosis by compound 11a at >1 mu M concentrations of compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.103
• 作为产物：
  描述：

  、 萘-2-甲胺 在 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 benzyl (S)-5-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-6-((naphthalen-2-ylmethyl)amino)-6-oxohexanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors

  摘要：

  A series of boron peptides 11, 13, 15 and 17 were designed and synthesized as proteasome inhibitors based on the structure of Belactosin C. Matteson homologation was a key step in the synthesis of the boron peptides. Compounds 11a and 13 showed significant inhibition of 20S proteasome chymotrypsin-like (beta 5) activity (IC(50) = 0.28 and 0.51 mu M, respectively). Furthermore, like PS-341, compound 11a increased the G2/M cell distribution. A biparametric cytofluorimetric analysis with FITC-labeled annexin V and propidium iodide showed induction of apoptosis by compound 11a at >1 mu M concentrations of compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.103