1-methyl-4-{[({[({[({[(1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxylic acid | 295805-54-8

• 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: 1-methyl-4-{[({[({[({[(1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxylic acid
• CAS: 295805-54-8
• 化学式: C₃₀H₃₁N₉O₆
• 分子量: 613.633
• InChiKey: VFAVKOZGKXDJGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  288.7 °C
• 沸点：
  676.6±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  178.35
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-methyl-4-{[({[({[({[(1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxylic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N-[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carboxamide
  参考文献：
  名称：

  Facile synthesis of oligopeptide distamycin analogs devoid of hydrogen bond donors or acceptors at the N-terminus: sequence-specific duplex DNA binding as a function of peptide chain length

  摘要：

  The first examples of distamycin analogs, which lack hydrogen bond interactor groups at the N-terminus, have been synthesized. The bispyrrole peptide did not exhibit any detectable binding with double-stranded (ds) DNA. However, all other homologues did bind to ds-DNA strongly, with the binding affinities increasing as a function of the number of repeating pyrrole carboxamide units, implying that a hydrogen bond donor or acceptor atom per se at the N-terminus is not essential for their DNA binding. Studies with poly d(GC) showed that the N-terminal formamide is not a prerequisite for GC binding, contrary to earlier postulations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00802-9
• 作为产物：
  描述：

  H-Py-Py-Py-OMe hydrochloride 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， -5.0~20.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 1-methyl-4-{[({[({[({[(1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Facile synthesis of oligopeptide distamycin analogs devoid of hydrogen bond donors or acceptors at the N-terminus: sequence-specific duplex DNA binding as a function of peptide chain length

  摘要：

  The first examples of distamycin analogs, which lack hydrogen bond interactor groups at the N-terminus, have been synthesized. The bispyrrole peptide did not exhibit any detectable binding with double-stranded (ds) DNA. However, all other homologues did bind to ds-DNA strongly, with the binding affinities increasing as a function of the number of repeating pyrrole carboxamide units, implying that a hydrogen bond donor or acceptor atom per se at the N-terminus is not essential for their DNA binding. Studies with poly d(GC) showed that the N-terminal formamide is not a prerequisite for GC binding, contrary to earlier postulations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00802-9

文献信息

• Distamycin Analogues without Leading Amide at Their N-Termini − Comparative Binding Properties to AT- and GC-Rich DNA Sequences
  作者：Mini Thomas、Umesh Varshney、Santanu Bhattacharya

  DOI：10.1002/1099-0690(200211)2002:21<3604::aid-ejoc3604>3.0.co;2-x

  日期：2002.11