tert-butyl (S)-4-(3-(1-(1-(tert-butoxy)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-1H-1,2,3-triazol-4-yl)-5-ethynylbenzoyl)piperazine-1-carboxylate | 1262483-39-5

• 分子结构分类: 有机化合物
• 英文名称: tert-butyl (S)-4-(3-(1-(1-(tert-butoxy)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-1H-1,2,3-triazol-4-yl)-5-ethynylbenzoyl)piperazine-1-carboxylate
• CAS: 1262483-39-5
• 化学式: C₃₃H₃₉N₅O₆
• 分子量: 601.703
• InChiKey: OJXZVSYZMBAXOT-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  44.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127.09
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-4-(3-(1-(1-(tert-butoxy)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-1H-1,2,3-triazol-4-yl)-5-ethynylbenzoyl)piperazine-1-carboxylate 、 methyl (2S)-2-azido-3-hydroxypropanoate 在 铜 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 以67%的产率得到tert-butyl 4-[3-[1-[(2S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl]triazol-4-yl]-5-[1-[(2S)-3-(4-hydroxyphenyl)-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]triazol-4-yl]benzoyl]piperazine-1-carboxylate
  参考文献：
  名称：

  Universal Peptidomimetics

  摘要：

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.

  DOI：

  10.1021/ja1071916
• 作为产物：
  描述：

  3-bromo-5-iodobenzoyl chloride 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 水 、 铜 、 copper(II) sulfate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 42.17h， 生成 tert-butyl (S)-4-(3-(1-(1-(tert-butoxy)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-1H-1,2,3-triazol-4-yl)-5-ethynylbenzoyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Universal Peptidomimetics

  摘要：

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.

  DOI：

  10.1021/ja1071916