ethyl 4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-1-methylpyrrole-2-acrylate | 296789-18-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-1-methylpyrrole-2-acrylate
• 英文别名: ethyl (E)-3-[4-[(4-acetamido-1-methylimidazole-2-carbonyl)amino]-1-methylpyrrol-2-yl]prop-2-enoate
• CAS: 296789-18-9
• 化学式: C₁₇H₂₁N₅O₄
• 分子量: 359.385
• InChiKey: CYMDNEMFKKVZOP-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-1-methylpyrrole-2-acrylate 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 AcImPyLCOCPI
  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 manganese(IV) oxide 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 ethyl 4-[[4-(acetylamino)-1-methylimidazol-2-yl]carbonylamino]-1-methylpyrrole-2-acrylate
  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

文献信息

• Highly Cooperative DNA Dialkylation by the Homodimer of Imidazole−Pyrrole Diamide−CPI Conjugate with Vinyl Linker
  作者：Zhi-Fu Tao、Isao Saito、Hiroshi Sugiyama

  DOI：10.1021/ja9926212

  日期：2000.3.1

  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.