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}-1-H-pyrrole-2-carboxylic acid | 295805-53-7

• 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}-1-H-pyrrole-2-carboxylic acid
• 英文别名: 1-methyl-4-{[4-({4-[(1-methylpyrrole-2-yl)carbonyl]amino-1-methylpyrrole-2-yl}carbonyl)amino-1-methylpyrrole-2-yl]carbonyl}aminopyrrole-2-carboxylic acid；1-Methyl-4-[[1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carbonyl]amino]pyrrole-2-carboxylic acid
• CAS: 295805-53-7
• 化学式: C₂₄H₂₅N₇O₅
• 分子量: 491.506
• InChiKey: JIUCPRRWFCILIU-UHFFFAOYSA-N

物化性质

• 熔点：
  175.6 °C
• 沸点：
  590.8±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  5

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}-1-H-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 SL 11055
  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 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 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}-1-H-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

• Facile synthesis of novel fluorescent distamycin analogues
  作者：Santanu Bhattacharya、Mini Thomas

  DOI：10.1016/s0040-4039(01)01040-1

  日期：2001.8

  A facile synthesis of four distamycin analogues that bear the dansyl fluorophore is described. The nature of the linkage between the fluorophore and the sequence recognition element had a dramatic effect on the fluorescence properties of these ligands upon DNA binding.

  描述了一种带有丹磺酰基荧光团的四种间他霉素类似物的简便合成方法。荧光基团和序列识别元件之间的连接性质对DNA结合后的这些配体的荧光性质产生了显着影响。
• 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
• Novel distamycin analogues: facile synthesis of cholesterol conjugates of distamycin-like oligopeptides
  作者：Santanu Bhattacharya、Mini Thomas

  DOI：10.1016/s0040-4039(01)00489-0

  日期：2001.5

  A facile route towards the synthesis of the first examples of cholesterol-conjugated distamycin analogues is described. These compounds retain their strong binding capacity to double-stranded (ds)-DNA. Aqueous suspensions of these analogues exhibited closed, vesicle-like structures under transmission electron microscope. (C) 2001 Published by Elsevier Science Ltd.
• WO2007/29364
  申请人：——

  公开号：——

  公开（公告）日：——