ethyl (E)-3-[(3S)-2-[(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-2-[(3-hydroxy-2-methylbenzoyl)amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]-3,4-dihydro-1H-isoquinolin-3-yl]prop-2-enoate | 1050655-55-4

• 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: ethyl (E)-3-[(3S)-2-[(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-2-[(3-hydroxy-2-methylbenzoyl)amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]-3,4-dihydro-1H-isoquinolin-3-yl]prop-2-enoate
• CAS: 1050655-55-4
• 化学式: C₃₆H₄₈N₄O₈
• 分子量: 664.799
• InChiKey: KBQFRFGWXLHLMD-OZKRFPBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  174
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  、 2-甲基-3-羟基苯甲酸 在 三氟乙酸 、 N-甲基吗啉 、 water soluble carbodiimide 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 ethyl (E)-3-[(3S)-2-[(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-2-[(3-hydroxy-2-methylbenzoyl)amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]-3,4-dihydro-1H-isoquinolin-3-yl]prop-2-enoate
  参考文献：
  名称：

  C-terminal constrained phenylalanine as a pharmacophoric unit in peptide-based proteasome inhibitors

  摘要：

  Here we report the synthesis and biological properties of peptide-based molecules bearing constrained analogues of phenylalanine at the C-terminal. Compounds were tested as proteasome subunits' inhibitors. Dehydro-peptides showed good inhibition, in particular against trypsin-like (T-L) proteasome activity while some C-terminal Tic-derivatives inhibit only caspase-like activity in enzymatic beta 1 subunits with a certain degree of efficacy. The best analogues of the series demonstrated good resistance to proteolysis and a capacity to permeate the cell membrane. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.002

文献信息

• C-terminal constrained phenylalanine as a pharmacophoric unit in peptide-based proteasome inhibitors
  作者：Anna Baldisserotto、Mauro Marastoni、Ilaria Lazzari、Claudio Trapella、Riccardo Gavioli、Roberto Tomatis

  DOI：10.1016/j.ejmech.2007.10.002

  日期：2008.7

  Here we report the synthesis and biological properties of peptide-based molecules bearing constrained analogues of phenylalanine at the C-terminal. Compounds were tested as proteasome subunits' inhibitors. Dehydro-peptides showed good inhibition, in particular against trypsin-like (T-L) proteasome activity while some C-terminal Tic-derivatives inhibit only caspase-like activity in enzymatic beta 1 subunits with a certain degree of efficacy. The best analogues of the series demonstrated good resistance to proteolysis and a capacity to permeate the cell membrane. (c) 2007 Elsevier Masson SAS. All rights reserved.