tert-butyl ((S)-1-((S)-3-(((S)-6-(benzylamino)-5-(((benzyloxy)carbonyl)amino)-6-oxohexyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropan-2-yl)carbamate | 936835-82-4

• 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: tert-butyl ((S)-1-((S)-3-(((S)-6-(benzylamino)-5-(((benzyloxy)carbonyl)amino)-6-oxohexyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropan-2-yl)carbamate
• CAS: 936835-82-4
• 化学式: C₄₇H₅₇N₅O₈
• 分子量: 819.998
• InChiKey: PEQASRMSIPJLPI-YKXUKSTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  60.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  175.4
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((S)-1-((S)-3-(((S)-6-(benzylamino)-5-(((benzyloxy)carbonyl)amino)-6-oxohexyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropan-2-yl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到
  参考文献：
  名称：

  Further studies on the effect of lysine at the C-terminus of the Dmt-Tic opioid pharmacophore

  摘要：

  A wide range of activities are induced by Lys when introduced at C-terminus of the delta-opioid Dmt-Tic pharmacophore through the alpha-amine group, including: improved delta-antagonism, mu-agonism and p-antagonism. Here we report the synthesis of a new series of compounds with the general formula H-Dmt-Tic-NH-(CH2)(4)-CH(R)-R' (R = -NH2, -NH-Ac, -NH-Z; R'= CO-NH-Ph, -CO-NH-CH2-Ph, -Bid) in which Lys is linked to Dint-Tic through its side-chain amine group. All new compounds (1-9) displayed potent and selective delta-antagonism (MVD, pA(2) = 7.81-8.27), which was independent of the functionalized alpha-amine and carboxylic groups of C-terminal Lys. This behaviour suggests a direct application as a prototype intermediate, such as Boc-Dmt-Tic-epsilon-Lys(Z)OMe, which could be successfully applied in the synthesis (after Z or methyl ester removal) of unique designed multiple ligands containing the pharmacophore of the quintessential delta-antagonist Dmt-Tic and another opioid or biologically active non-opioid ligand. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.039
• 作为产物：
  描述：

  、 N-Boc-2,6-二甲基-L-酪氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以87%的产率得到tert-butyl ((S)-1-((S)-3-(((S)-6-(benzylamino)-5-(((benzyloxy)carbonyl)amino)-6-oxohexyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Further studies on the effect of lysine at the C-terminus of the Dmt-Tic opioid pharmacophore

  摘要：

  A wide range of activities are induced by Lys when introduced at C-terminus of the delta-opioid Dmt-Tic pharmacophore through the alpha-amine group, including: improved delta-antagonism, mu-agonism and p-antagonism. Here we report the synthesis of a new series of compounds with the general formula H-Dmt-Tic-NH-(CH2)(4)-CH(R)-R' (R = -NH2, -NH-Ac, -NH-Z; R'= CO-NH-Ph, -CO-NH-CH2-Ph, -Bid) in which Lys is linked to Dint-Tic through its side-chain amine group. All new compounds (1-9) displayed potent and selective delta-antagonism (MVD, pA(2) = 7.81-8.27), which was independent of the functionalized alpha-amine and carboxylic groups of C-terminal Lys. This behaviour suggests a direct application as a prototype intermediate, such as Boc-Dmt-Tic-epsilon-Lys(Z)OMe, which could be successfully applied in the synthesis (after Z or methyl ester removal) of unique designed multiple ligands containing the pharmacophore of the quintessential delta-antagonist Dmt-Tic and another opioid or biologically active non-opioid ligand. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.039