tert-butyl (R,E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1050655-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: tert-butyl (R,E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS: 1050655-41-8
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: SOWNZVJAHKXRIX-OFAQMXQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (R,E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 、 BOC-L-丝氨酸 在 三氟乙酸 、 N-甲基吗啉 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成
  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
• 作为产物：
  描述：

  (R)-3-甲酰基-3,4-二氢-1H-异喹啉-2-羧酸叔丁酯 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到tert-butyl (R,E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
  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