(2S)-4-methyl-2-[4-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]triazol-1-yl]pentanoic acid | 1454659-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-4-methyl-2-[4-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]triazol-1-yl]pentanoic acid
• CAS: 1454659-70-1
• 化学式: C₂₁H₃₀N₄O₄
• 分子量: 402.494
• InChiKey: HTMWRNQSFSJACG-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  106.34
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 (2S)-4-methyl-2-[4-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]triazol-1-yl]pentanoic acid 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以59%的产率得到(2S)-2-[4-[(1S)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenylethyl]triazol-1-yl]-4-methylpentanoic acid
  参考文献：
  名称：

  Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity

  摘要：

  Using Cu(I)-catalyzed azide-alkyne cycloaddition in a mixed classical organic phase and solid phase peptide synthesis approach, we synthesized four analogs of Leu-enkephalin to systematically replace amides by 1,4-disubstituted[1,2,3] triazoles. The peptidomimetics obtained were characterized by competitive binding, contractility assays and ERK1/2 phosphorylation. The present study reveals that the analog bearing a triazole between Phe and Leu retains some potency, more than all the others, suggesting that the hydrogen bond acceptor capacity of the last amide of Leu-enkephalin is essential for the biological activity of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.020
• 作为产物：
  描述：

  L-亮氨酸 在 triflic azide 、 2,6-二甲基吡啶 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 32.0h， 生成 (2S)-4-methyl-2-[4-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]triazol-1-yl]pentanoic acid
  参考文献：
  名称：

  Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity

  摘要：

  Using Cu(I)-catalyzed azide-alkyne cycloaddition in a mixed classical organic phase and solid phase peptide synthesis approach, we synthesized four analogs of Leu-enkephalin to systematically replace amides by 1,4-disubstituted[1,2,3] triazoles. The peptidomimetics obtained were characterized by competitive binding, contractility assays and ERK1/2 phosphorylation. The present study reveals that the analog bearing a triazole between Phe and Leu retains some potency, more than all the others, suggesting that the hydrogen bond acceptor capacity of the last amide of Leu-enkephalin is essential for the biological activity of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.020