N-(tert-butoxycarbonyl)-L-isoleucyl-N1-[(1S)-2-azido-1-methylethyl]-N2-(2,4-dimethoxybenzyl)-2-methylalaninamide | 1316672-53-3

• 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: N-(tert-butoxycarbonyl)-L-isoleucyl-N1-[(1S)-2-azido-1-methylethyl]-N2-(2,4-dimethoxybenzyl)-2-methylalaninamide
• 英文别名: tert-butyl N-[(2S,3S)-1-[[1-[[(2S)-1-azidopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]-[(2,4-dimethoxyphenyl)methyl]amino]-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 1316672-53-3
• 化学式: C₂₇H₄₄N₆O₆
• 分子量: 548.683
• InChiKey: DWQZGBKXCAIMAE-SPEDKVCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-L-isoleucyl-N1-[(1S)-2-azido-1-methylethyl]-N2-(2,4-dimethoxybenzyl)-2-methylalaninamide 、 prop-2-yn-1-yl 3α,5β-{[(prop-2-yn-1-yloxy)acetyl]oxy}cholan-24-oate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 以62%的产率得到[1-[(2S)-2-[[2-[(2,4-dimethoxyphenyl)methyl-[(2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-2-methylpropanoyl]amino]propyl]triazol-4-yl]methyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[2-[[1-[(2S)-2-[[2-[(2,4-dimethoxyphenyl)methyl-[(2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-2-methylpropanoyl]amino]propyl]triazol-4-yl]methoxy]acetyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Design and synthesis of bile acid–peptide conjugates linked via triazole moiety

  摘要：

  通过 Cu（I）催化的点击化学，描述了胆汁酸与肽的共轭。利用 Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click "反应)，合成了基于胆酸、去氧胆酸和石胆酸衍生物的通过 1,2,3- 三唑分子连接的新型胆酸肽共轭物。研究表明，多达三个肽片段可以连接到一个中央甾体核心，从而形成复杂的三维多共轭结构，在生物化学、药物化学和配位化学中具有重要的应用价值。

  DOI：

  10.1039/c0ob01188f
• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 (S)-1-azido-2-isocyanopropane 、 2,4-二甲氧基苯甲胺 、 丙酮 以 甲醇 为溶剂， 反应 24.0h， 以55%的产率得到N-(tert-butoxycarbonyl)-L-isoleucyl-N1-[(1S)-2-azido-1-methylethyl]-N2-(2,4-dimethoxybenzyl)-2-methylalaninamide
  参考文献：
  名称：

  Design and synthesis of bile acid–peptide conjugates linked via triazole moiety

  摘要：

  通过 Cu（I）催化的点击化学，描述了胆汁酸与肽的共轭。利用 Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click "反应)，合成了基于胆酸、去氧胆酸和石胆酸衍生物的通过 1,2,3- 三唑分子连接的新型胆酸肽共轭物。研究表明，多达三个肽片段可以连接到一个中央甾体核心，从而形成复杂的三维多共轭结构，在生物化学、药物化学和配位化学中具有重要的应用价值。

  DOI：

  10.1039/c0ob01188f

文献信息

• Synthesis of new betulinic acid–peptide conjugates and in vivo and in silico studies of the influence of peptide moieties on the triterpenoid core activity
  作者：Anastasiya I. Govdi、Nadezda V. Sokolova、Irina V. Sorokina、Dmitry S. Baev、Tatyana G. Tolstikova、Victor I. Mamatyuk、Dmitry S. Fadeev、Sergey F. Vasilevsky、Valentine G. Nenajdenko

  DOI：10.1039/c4md00236a

  日期：——

  Betulinic acid–peptide conjugates exhibit high anti-inflammatory activity.

  白桦酸-肽共轭物表现出很高的抗炎活性。
• Synthesis and biological activity of <i>N</i>-substituted-tetrahydro-γ-carbolines containing peptide residues
  作者：Nadezhda V Sokolova、Valentine G Nenajdenko、Vladimir B Sokolov、Daria V Vinogradova、Elena F Shevtsova、Ludmila G Dubova、Sergey O Bachurin

  DOI：10.3762/bjoc.10.13

  日期：——

  The synthesis of novel peptide conjugates of N-substituted-tetrahydro-gamma-carbolines has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained gamma-carboline-peptide conjugates on the rat liver mitochondria was evaluated. It was found that all compounds in the concentration of 30 microM did onot induce depolarization of mitochondria

  N-取代-四氢-γ-咔啉的新型肽缀合物的合成已使用 Ugi 多组分反应和 Cu (I) 催化点击化学的序列进行。评估了获得的γ-咔啉-肽缀合物对大鼠肝线粒体的影响。发现30μM浓度的所有化合物均不诱导线粒体去极化，但对线粒体通透性转变具有一定的抑制作用。含有末端炔基的原始 N-取代四氢-γ-咔啉表现出很高的促氧化活性，而它们与肽片段的结合物略微抑制了自氧化和 t-BHP 诱导的脂质过氧化。
• Synthesis and testing of trifluoromethyl-containing phosphonate–peptide conjugates as inhibitors of serine hydrolases
  作者：Nadezhda V. Sokolova、Valentine G. Nenajdenko、Vladimir B. Sokolov、Olga G. Serebryakova、Galina F. Makhaeva

  DOI：10.1016/j.bmcl.2011.09.030

  日期：2011.12

  A modification of novel fluorinated organophosphorous compounds containing terminal alkyne group by different azidopeptides via Cu(I)-catalyzed click chemistry has been described. The inhibitor activity of trifluoromethyl-containing methylphosphonates and their peptide-conjugates towards acetylcholinesterase, butyrylcholinesterase, and carboxylesterase has been investigated. It was shown that the incorporation of peptide fragments significantly modulates the esterase profile of starting methylphosphonates. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence
  作者：Daria V. Vorobyeva、Nadezhda V. Sokolova、Valentine G. Nenajdenko、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1016/j.tet.2011.11.037

  日期：2012.1

  A convenient synthetic pathway to novel functionalized tetrapeptides containing the 1,2,3-triazole moiety is described. The target molecules were obtained by the reaction of fluorinated alpha-amino acids or alpha-aminophosphonates with azidopeptides via Cu(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). The synthesized tetrapeptides may find important applications in biomedical chemistry as potential drugs. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of peptide conjugates of mestranol by a 1,3-dipolar cycloaddition click reaction
  作者：N. V. Sokolova、V. G. Nenajdenko

  DOI：10.1007/s10593-012-1074-3

  日期：2012.9

  An efficient method is presented for the synthesis of a series of peptide conjugates of the ethynylestradiol 3-methyl ether and the corresponding azidopeptides by a copper(I)-catalyzed 1,3-di-polar cycloaddition click reaction.