3'-<4-(N-methyl-4-nitropyrrole-2-carboxamido)-N-methylpyrrole-2-carboxamido>-3-methyldipropylamine | 144181-96-4

• 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: 3'-<4-(N-methyl-4-nitropyrrole-2-carboxamido)-N-methylpyrrole-2-carboxamido>-3-methyldipropylamine
• CAS: 144181-96-4
• 化学式: C₂₄H₃₇N₇O₆
• 分子量: 519.601
• InChiKey: JJLHMVVBGSHAEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  152.77
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-<4-(N-methyl-4-nitropyrrole-2-carboxamido)-N-methylpyrrole-2-carboxamido>-3-methyldipropylamine 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、2.07 MPa 条件下， 反应 17.42h， 生成 1-Methyl-1H-imidazole-2-carboxylic acid [5-(5-{3-[(3-amino-propyl)-methyl-amino]-propylcarbamoyl}-1-methyl-1H-pyrrol-3-ylcarbamoyl)-1-methyl-1H-pyrrol-3-yl]-amide
  参考文献：
  名称：

  Design of peptides that bind in the minor groove of DNA at 5'-(A,T)G(A,T)C(A,T)-3' sequences by a dimeric side-by-side motif

  摘要：

  The designed peptides pyridine-2-carboxamide-netropsin (2-PyN) and 1-methylimidazole-2-carboxamide-netropsin (2-ImN) are crescent-shaped synthetic analogs of the natural products netropsin (N) and distamycin A (D). Footprinting experiments indicate that the peptides 2-PyN and 2-ImN bind specifically the 5 base pair sequence 5'-TGTCA-3'. Affinity cleaving data suggest that the complexes, 2-ImN.5'-TGTCA-3' and 2-PyN.5'-TGTCA-3', are composed of two equivalent orientations which disfavor a 1:1 model. The footprinting and affinity cleaving data are in accord with a 2:1 complex where a novel side-by-side antiparallel dimer binds in the minor groove of double-helical DNA.

  DOI：

  10.1021/ja00049a006
• 作为产物：
  描述：

  1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid 、 tert-butyl (3-((3-aminopropyl)(methyl)amino)propyl)carbamate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以78%的产率得到3'-<4-(N-methyl-4-nitropyrrole-2-carboxamido)-N-methylpyrrole-2-carboxamido>-3-methyldipropylamine
  参考文献：
  名称：

  Design of peptides that bind in the minor groove of DNA at 5'-(A,T)G(A,T)C(A,T)-3' sequences by a dimeric side-by-side motif

  摘要：

  The designed peptides pyridine-2-carboxamide-netropsin (2-PyN) and 1-methylimidazole-2-carboxamide-netropsin (2-ImN) are crescent-shaped synthetic analogs of the natural products netropsin (N) and distamycin A (D). Footprinting experiments indicate that the peptides 2-PyN and 2-ImN bind specifically the 5 base pair sequence 5'-TGTCA-3'. Affinity cleaving data suggest that the complexes, 2-ImN.5'-TGTCA-3' and 2-PyN.5'-TGTCA-3', are composed of two equivalent orientations which disfavor a 1:1 model. The footprinting and affinity cleaving data are in accord with a 2:1 complex where a novel side-by-side antiparallel dimer binds in the minor groove of double-helical DNA.

  DOI：

  10.1021/ja00049a006