N2-((benzyloxy)carbonyl)-N6-((S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-lysine | 936835-78-8

• 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: N2-((benzyloxy)carbonyl)-N6-((S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-lysine
• CAS: 936835-78-8
• 化学式: C₂₉H₃₇N₃O₇
• 分子量: 539.629
• InChiKey: ZUPHQOBZISDIIH-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  134.27
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N2-((benzyloxy)carbonyl)-N6-((S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-lysine 在 N-甲基吗啉 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成
  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：

  Boc-Tic-ε-Lys(Z)-OMe 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以81%的产率得到N2-((benzyloxy)carbonyl)-N6-((S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-lysine
  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