4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-2-hydroxymethyl-1-methylpyrrole | 263710-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-2-hydroxymethyl-1-methylpyrrole
• CAS: 263710-64-1
• 化学式: C₁₃H₁₇N₅O₃
• 分子量: 291.31
• InChiKey: ZPEPEOUENFFKES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101.18
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-2-hydroxymethyl-1-methylpyrrole 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-1-methylpyrrole-2-aldehyde
  参考文献：
  名称：

  Highly Cooperative DNA Dialkylation by the Homodimer of Imidazole−Pyrrole Diamide−CPI Conjugate with Vinyl Linker

  摘要：

  We synthesized new type of diamide-CPI conjugate possessing a vinyl linker, 7. Sequence-selective alkylation of double-stranded DNA by 7 was investigated by high-resolution denaturing get electrophoresis using similar to 400 bp DNA fragments. Highly efficient alkylation predominantly occurs simultaneously at the purines of 5'-PyG(AIT)CPu-3' site on both strands at a nanomolar concentration of 7. These results suggest that the homodimer of conjugate 7 dialkylates both strands according to Dervan's pairing rule together with a new mode of recognition in which the Im-vinyl linker (L) pair targets G/C base pairs. In addition to the major dialkylation sites, a minor alkylation site was also observed at 5'-GT(PST)GC-3'. This alkylation can be explained by an analogous slipped homodimer recognition mode in which the L-L pair recognizes the A/T base pair. Efficient dialkylation by the homodimer of 7 was further confirmed using oligonucleotides (ODNs). HPLC analysis revealed that the conjugate 7 simultaneously alkylates GN3/AN3 of the target sequences on both strands of ODNs.

  DOI：

  10.1021/ja9926212
• 作为产物：
  描述：

  4-[(4-Acetylamino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以47.4%的产率得到4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-2-hydroxymethyl-1-methylpyrrole
  参考文献：
  名称：

  Highly Cooperative DNA Dialkylation by the Homodimer of Imidazole−Pyrrole Diamide−CPI Conjugate with Vinyl Linker

  摘要：

  We synthesized new type of diamide-CPI conjugate possessing a vinyl linker, 7. Sequence-selective alkylation of double-stranded DNA by 7 was investigated by high-resolution denaturing get electrophoresis using similar to 400 bp DNA fragments. Highly efficient alkylation predominantly occurs simultaneously at the purines of 5'-PyG(AIT)CPu-3' site on both strands at a nanomolar concentration of 7. These results suggest that the homodimer of conjugate 7 dialkylates both strands according to Dervan's pairing rule together with a new mode of recognition in which the Im-vinyl linker (L) pair targets G/C base pairs. In addition to the major dialkylation sites, a minor alkylation site was also observed at 5'-GT(PST)GC-3'. This alkylation can be explained by an analogous slipped homodimer recognition mode in which the L-L pair recognizes the A/T base pair. Efficient dialkylation by the homodimer of 7 was further confirmed using oligonucleotides (ODNs). HPLC analysis revealed that the conjugate 7 simultaneously alkylates GN3/AN3 of the target sequences on both strands of ODNs.

  DOI：

  10.1021/ja9926212