N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide | 1360157-19-2

• 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: N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide
• 英文别名: N,N-bis[(2,4-dimethoxyphenyl)methyl]-1H-imidazole-5-sulfonamide
• CAS: 1360157-19-2
• 化学式: C₂₁H₂₅N₃O₆S
• 分子量: 447.512
• InChiKey: CWMJBNKALRXHEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.99h， 生成 N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide
  参考文献：
  名称：

  Design and Synthesis of an Fmoc-SPPS-Compatible Amino Acid Building Block Mimicking the Transition State of Phosphohistidine Phosphatase

  摘要：

  The synthesis of a sulfonamide-based transition-state (TS) analogue of enzymatic phosphohistidine dephosphorylation as an amino acid building block is presented, together with the proof-of-concept of its incorporation into peptides. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The peptides are designed as inhibitors of phosphohistidine phosphatase and as a pull-down probe for identification of phosphohistidine phosphatases, respectively.

  DOI：

  10.1021/jo2025702
• 作为产物：
  描述：

  双(2,4-二甲氧基苄基)胺 、 咪唑-4-磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以90%的产率得到N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide
  参考文献：
  名称：

  Design and Synthesis of an Fmoc-SPPS-Compatible Amino Acid Building Block Mimicking the Transition State of Phosphohistidine Phosphatase

  摘要：

  The synthesis of a sulfonamide-based transition-state (TS) analogue of enzymatic phosphohistidine dephosphorylation as an amino acid building block is presented, together with the proof-of-concept of its incorporation into peptides. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The peptides are designed as inhibitors of phosphohistidine phosphatase and as a pull-down probe for identification of phosphohistidine phosphatases, respectively.

  DOI：

  10.1021/jo2025702

文献信息

• Design and Synthesis of an Fmoc-SPPS-Compatible Amino Acid Building Block Mimicking the Transition State of Phosphohistidine Phosphatase
  作者：Martijn F. Eerland、Christian Hedberg

  DOI：10.1021/jo2025702

  日期：2012.2.17

  The synthesis of a sulfonamide-based transition-state (TS) analogue of enzymatic phosphohistidine dephosphorylation as an amino acid building block is presented, together with the proof-of-concept of its incorporation into peptides. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The peptides are designed as inhibitors of phosphohistidine phosphatase and as a pull-down probe for identification of phosphohistidine phosphatases, respectively.