2-pentafluorophenoxycarbonyl-1-methyl-4-{3-(1-methylimidazole-2-carboxamido)propanamido}pyrrole

• 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: 2-pentafluorophenoxycarbonyl-1-methyl-4-{3-(1-methylimidazole-2-carboxamido)propanamido}pyrrole
• 英文别名: 2-pentafluorophenoxycarbonyl-1-methyl-4-{3-(1-methyimidazole-2-carboxamido)propanamido}pyrrole；(2,3,4,5,6-Pentafluorophenyl) 1-methyl-4-[3-[(1-methylimidazole-2-carbonyl)amino]propanoylamino]pyrrole-2-carboxylate
• 化学式: C₂₀H₁₆F₅N₅O₄
• 分子量: 485.37
• InChiKey: RNDDUQHPIWPWFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  乙基4-氨基-1-甲基-1H-吡咯-2-羧酸酯 在 吡啶 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-pentafluorophenoxycarbonyl-1-methyl-4-{3-(1-methylimidazole-2-carboxamido)propanamido}pyrrole
  参考文献：
  名称：

  Use of Ferrocene Scaffolds as Pendant Groups in Hairpin-Type Pyrrole-Imidazole Polyamide Molecules Showing Sequence-Selective Binding to DNA Duplexes

  摘要：

  The synthesis and properties of new cotljugate molecules, Fc-PIA, composed of ferrocene (Fc) and pyrrole-imidazole polyamides (PIA) are reported. As a PIA sequence, we chose Im-Py-Im/Py-Im-Py considering its future application to the SNPs detection of genes having a GCG/CGC sequence. Two types of Fc-containing linkers, i.e., ferrocene-1,1'-dicarboxamide and ferrocenecarboxamide, were designed, and several Fc-PIPA molecules having these linkers were synthesized. Titration studies by use of circular dichroism revealed that the carboxamide-type Fc-PIA could bind to the target DNA with an association constant of 10(7) M-1. In contrast, ferrocene dicarboxamide-type compounds have slightly weaker affinity for the target DNA. However, the affinity could be recovered by replacing one of the pyrrole residues with beta-alanine. We carried out the CV measurement and observed quasi-irreversible oxidation of the ferrocene moieties in the Fc-PIA compounds. These properties of Fc-PIA indicate the potential usefulness of these molecules in electrochemical detection of genes.

  DOI：

  10.1021/jo051247n

文献信息

• EP1719777
  申请人：——

  公开号：——

  公开（公告）日：——