N-[5-[[5-(3-二甲基氨基丙基氨基甲酰)-1-甲基吡咯-3-基]氨基甲酰]-1-甲基吡咯-3-基]-1-甲基咪唑-2-甲酰胺 | 129601-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 中文名称: N-[5-[[5-(3-二甲基氨基丙基氨基甲酰)-1-甲基吡咯-3-基]氨基甲酰]-1-甲基吡咯-3-基]-1-甲基咪唑-2-甲酰胺
• 英文名称: N-<5-<<(3,3-dimethylaminopropyl)amino>carbonyl>-1-methyl-1H-pyrrol-3-yl>-4-<<<1-methyl-1H-imidazol-2-yl>carbonyl>amino>-1-methyl-1H-pyrrole-2-carboxamide
• 英文别名: 1-Methylimidazole-2-carboxamide netropsin；N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylimidazole-2-carboxamide
• CAS: 129601-50-9
• 化学式: C₂₂H₃₀N₈O₃
• 分子量: 454.532
• InChiKey: DMOMFSUPEGKPKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[3-(dimethylamino)propyl]-1-methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxamide 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 N-[5-[[5-(3-二甲基氨基丙基氨基甲酰)-1-甲基吡咯-3-基]氨基甲酰]-1-甲基吡咯-3-基]-1-甲基咪唑-2-甲酰胺
  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

文献信息

• 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
  作者：Warren S. Wade、Milan Mrksich、Peter B. Dervan

  DOI：10.1021/ja00049a006

  日期：1992.11

  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.
• Chen, Yong-Huang; Lown, J. William, Heterocycles, 1995, vol. 41, # 8, p. 1691 - 1708
  作者：Chen, Yong-Huang、Lown, J. William

  DOI：——

  日期：——