2-ethoxycarbonyl-1-methyl-4-{3-(1-methylimidazole-2-carboxamido)propanamido}pyrrole | 865307-77-3

• 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-ethoxycarbonyl-1-methyl-4-{3-(1-methylimidazole-2-carboxamido)propanamido}pyrrole
• 英文别名: 2-ethoxycarbonyl-1-methyl-4-{3-(1-methyimidazole-2-carboxamido)propanamido}pyrrole；Ethyl 1-methyl-4-[3-[(1-methylimidazole-2-carbonyl)amino]propanoylamino]pyrrole-2-carboxylate
• CAS: 865307-77-3
• 化学式: C₁₆H₂₁N₅O₄
• 分子量: 347.374
• InChiKey: ISWZIFRRYBZNSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethoxycarbonyl-1-methyl-4-{3-(1-methylimidazole-2-carboxamido)propanamido}pyrrole 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  乙基4-氨基-1-甲基-1H-吡咯-2-羧酸酯 在 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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-ethoxycarbonyl-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

• Electrochemically active ligand for sequence-specific detection of double-stranded nucleic acid molecule
  申请人：Sekine Mitsuo

  公开号：US20070172826A1

  公开（公告）日：2007-07-26

  The purpose of the present invention is to provide a compound that specifically binds to the base sequence of a double-stranded nucleic acid molecule. The compound can reduce the electrochemical signal/noise ratio (S/N) in electrochemical detection, and as a result, the detection sensitivity (precision) will be greatly improved so as to enable the determination of an ultratrace amount of nucleic acid molecule. The present invention relates to a ferrocene compound represented by the following general formula (I): wherein “A” represents a divalent ferrocene-containing linker or ferrocene-1,1′-yl, R 2 represents a hydrogen atom or alkyl; “n” and “m” represent any natural numbers; and “V” and “X” represent the pyrrole-imidazole-polyamide (PIPA); to a ligand consisting of said ferrocene compound for sequence-specific detection of double-stranded nucleic acid molecules; to a method for electrochemical detection of double-stranded nucleic acid molecules 8 with the use of said ligand; and to an apparatus or device for the electrochemical detection with the use of said ligand.

  本发明的目的是提供一种能够特异性结合双链核酸分子碱基序列的化合物。该化合物可降低电化学检测中的信号/噪声比（S/N），从而大大提高检测灵敏度（精度），使得能够确定极微量的核酸分子。本发明涉及一种由下述通式（I）表示的二茂铁化合物：其中“A”表示含二茂铁的二价连接基或二茂铁-1,1'-基，R2表示氢原子或烷基；“n”和“m”表示任意自然数；“V”和“X”表示吡咯-咪唑-多肽（PIPA）；以及利用该化合物制备的配体，用于序列特异性检测双链核酸分子、利用该配体进行电化学检测双链核酸分子的方法，以及利用该配体进行电化学检测的装置或设备。
• ELECTROCHEMICALLY ACTIVE LIGAND FOR SEQUENCE-SPECIFIC DETECTION OF DOUBLE-STRANDED NUCLEIC ACID MOLECULE
  申请人：Japan Science and Technology Agency

  公开号：EP1719777A1

  公开（公告）日：2006-11-08

  The purpose of the present invention is to provide a compound that specifically binds to the base sequence of a double-stranded nucleic acid molecule. The compound can reduce the electrochemical signal/noise ratio (S/N) in electrochemical detection, and as a result, the detection sensitivity (precision) will be greatly improved so as to enable the determination of an ultratrace amount of nucleic acid molecule. The present invention relates to a ferrocene compound represented by the following general formula (I): wherein "A" represents a divalent ferrocene-containing linker or ferrocene-1, 1'-yl, R2 represents a hydrogen atom or alkyl; "n" and "m" represent any natural numbers; and "V" and "X" represent the pyrrole-imidazole-polyamide (PIPA); to a ligand consisting of said ferrocene compound for sequence-specific detection of double-stranded nucleic acid molecules; to a method for electrochemical detection of double-stranded nucleic acid molecules 8 with the use of said ligand; and to an apparatus or device for the electrochemical detection with the use of said ligand.

  本发明的目的是提供一种能与双链核酸分子的碱基序列特异性结合的化合物。该化合物可以降低电化学检测中的电化学信噪比（S/N），从而大大提高检测灵敏度（精度），从而可以测定超微量的核酸分子。本发明涉及由以下通式（I）代表的二茂铁化合物： 其中 "A "代表含二茂铁的二价连接体或二茂铁-1，1'-基，R2代表氢原子或烷基；"n "和 "m "代表任何自然数；"V "和 "X "代表吡咯-咪唑-聚酰胺（PIPA）；由所述二茂铁化合物组成的用于序列特异性检测双链核酸分子的配体；使用所述配体对双链核酸分子进行电化学检测的方法；以及使用所述配体进行电化学检测的装置或设备。
• EP1719777
  申请人：——

  公开号：——

  公开（公告）日：——
• US7863455B2
  申请人：——

  公开号：US7863455B2

  公开（公告）日：2011-01-04
• Use of Ferrocene Scaffolds as Pendant Groups in Hairpin-Type Pyrrole-Imidazole Polyamide Molecules Showing Sequence-Selective Binding to DNA Duplexes
  作者：Kohji Seio、Masahiro Mizuta、Takeshi Terada、Mitsuo Sekine

  DOI：10.1021/jo051247n

  日期：2005.12.1

  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.