N-[3-(dimethylamino)propyl]-1-methyl-4-[[4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]-1H-pyrrole-2-carbonyl]amino]pyrrole-2-carboxamide | 913960-96-0

• 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-[3-(dimethylamino)propyl]-1-methyl-4-[[4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]-1H-pyrrole-2-carbonyl]amino]pyrrole-2-carboxamide
• CAS: 913960-96-0
• 化学式: C₂₂H₂₈N₈O₅
• 分子量: 484.515
• InChiKey: SPVFIMDSIYBMFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[3-(dimethylamino)propyl]-1-methyl-4-[[4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]-1H-pyrrole-2-carbonyl]amino]pyrrole-2-carboxamide 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 17.25h， 生成 (3-{4-[(4-Acetylamino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-2-[5-(3-dimethylamino-propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-pyrrol-1-yl}-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Toward encoding reactivity using double-stranded DNA. Sequence-dependent native chemical ligation of DNA binding polyamides

  摘要：

  The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated by dsDNAs containing ATTTTA or ATGTTA sites, the heterodimeric coupling between a tripyrrole and a polyamide equipped with two pyrroles and one imidazole, is accelerated by the latter DNA, but not by the other containing the A/T rich tract. These differences can be exploited for selecting preferred coupling pairs from a mixture of reactive monomers; therefore the reaction outcome depends on the instructions provided by the dsDNA sequence. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.126
• 作为产物：
  描述：

  3-(1-methyl-4-aminopyrrole-2-carbonylamino)propyldimethylamine 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 氯磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.33h， 生成 N-[3-(dimethylamino)propyl]-1-methyl-4-[[4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]-1H-pyrrole-2-carbonyl]amino]pyrrole-2-carboxamide
  参考文献：
  名称：

  Modulating the Rate of a Native Ligation Coupling between Tripyrrole Derivatives by Using Specific dsDNA Sequences

  摘要：

  The intrinsic recognition code associated with dsDNA allows either accelerating or retarding of a native chemical ligation reaction between tripyrrole ligands. The rate changes most probably stem from the sequence-dependent characteristics of the dsDNA-ligand complexes.

  DOI：

  10.1021/ol061551i

文献信息

• Modulating the Rate of a Native Ligation Coupling between Tripyrrole Derivatives by Using Specific dsDNA Sequences
  作者：Verónica I. Dodero、Manuel Mosquera、Juan B. Blanco、Luis Castedo、José L. Mascareñas

  DOI：10.1021/ol061551i

  日期：2006.9.1

  The intrinsic recognition code associated with dsDNA allows either accelerating or retarding of a native chemical ligation reaction between tripyrrole ligands. The rate changes most probably stem from the sequence-dependent characteristics of the dsDNA-ligand complexes.
• Toward encoding reactivity using double-stranded DNA. Sequence-dependent native chemical ligation of DNA binding polyamides
  作者：Adrian Jiménez-Balsa、Verónica I. Dodero、José L. Mascareñas

  DOI：10.1016/j.tet.2013.05.126

  日期：2013.9

  The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated by dsDNAs containing ATTTTA or ATGTTA sites, the heterodimeric coupling between a tripyrrole and a polyamide equipped with two pyrroles and one imidazole, is accelerated by the latter DNA, but not by the other containing the A/T rich tract. These differences can be exploited for selecting preferred coupling pairs from a mixture of reactive monomers; therefore the reaction outcome depends on the instructions provided by the dsDNA sequence. (C) 2013 Elsevier Ltd. All rights reserved.