2-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethylamino}-1H-benzimidazole-5-carboxylic acid methyl ester | 848408-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethylamino}-1H-benzimidazole-5-carboxylic acid methyl ester
• CAS: 848408-63-9
• 化学式: C₂₅H₄₀N₆O₆
• 分子量: 520.629
• InChiKey: DKFDEVOSAQTKFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  146.91
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethylamino}-1H-benzimidazole-5-carboxylic acid methyl ester 在 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 2-[2-(bis-{2-[3-(2-nitrophenyl)thioureido]ethyl}amino)ethylamino]-3H-benzimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Metal-Free Catalysts for the Hydrolysis of RNA Derived from Guanidines, 2-Aminopyridines, and 2-Aminobenzimidazoles

  摘要：

  2-Aminopyridine and 2-aminobenzimidazole were chosen as structural analogues to substitute guanidinium groups in receptor molecules designed as phosphoryl transfer catalysts. Shifting the pK(a) of the guanidinium analogues toward 7 was expected to raise catalytic activities in aqueous buffer. Although the pK(a)'s of both heterocycles are similar (6.2 and 7.0), only 2-aminobenzimidazole led to active RNA cleavers. All cleavage assays were run with fluorescently labeled substrates and a DNA sequencer. RNase contaminations would degrade RNA enantioselectively. In contrast, achiral catalysts such as 9b and 10b necessarily induce identical cleavage patterns in RNA and its mirror image. This principle allowed us to safely rule out contamination effects in this study. The most active catalysts, tris(2-aminobenzimidazoles) 9b and 1 Ob, were shown by fluorescence correlation spectroscopy (FCS) to aggregate with oligonucleotides. However, at very low concentrations the compounds are still active in the nonaggregated state. Conjugates of 10b with antisense oligonucleotides or RNA binding peptides, therefore, will be promising candidates as site specific artificial ribonucleases.

  DOI：

  10.1021/ja0443934
• 作为产物：
  描述：

  三(2-氨基乙基)胺 在 咪唑 、 sulfur 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 2-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethylamino}-1H-benzimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Metal-Free Catalysts for the Hydrolysis of RNA Derived from Guanidines, 2-Aminopyridines, and 2-Aminobenzimidazoles

  摘要：

  2-Aminopyridine and 2-aminobenzimidazole were chosen as structural analogues to substitute guanidinium groups in receptor molecules designed as phosphoryl transfer catalysts. Shifting the pK(a) of the guanidinium analogues toward 7 was expected to raise catalytic activities in aqueous buffer. Although the pK(a)'s of both heterocycles are similar (6.2 and 7.0), only 2-aminobenzimidazole led to active RNA cleavers. All cleavage assays were run with fluorescently labeled substrates and a DNA sequencer. RNase contaminations would degrade RNA enantioselectively. In contrast, achiral catalysts such as 9b and 10b necessarily induce identical cleavage patterns in RNA and its mirror image. This principle allowed us to safely rule out contamination effects in this study. The most active catalysts, tris(2-aminobenzimidazoles) 9b and 1 Ob, were shown by fluorescence correlation spectroscopy (FCS) to aggregate with oligonucleotides. However, at very low concentrations the compounds are still active in the nonaggregated state. Conjugates of 10b with antisense oligonucleotides or RNA binding peptides, therefore, will be promising candidates as site specific artificial ribonucleases.

  DOI：

  10.1021/ja0443934

文献信息

• Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole)
  作者：Friederike Danneberg、Alice Ghidini、Plamena Dogandzhiyski、Elisabeth Kalden、Roger Strömberg、Michael W Göbel

  DOI：10.3762/bjoc.11.55

  日期：——

  Tris(2-aminobenzimidazole) conjugates with antisense oligonucleotides are effective site-specific RNA cleavers. Their mechanism of action is independent of metal ions. Here we investigate conjugates with peptide nucleic acids (PNA). RNA degradation occurs with similar rates and substrate specificities as in experiments with DNA conjugates we performed earlier. Although aggregation phenomena are observed in some cases, proper substrate recognition is not compromised. While our previous synthesis of 2-aminobenzimidazoles required an HgO induced cyclization step, a mercury free variant is described herein.

  Tris(2-氨基苯并咪唑)与反义寡核苷酸结合物是有效的特异位点RNA切割酶。它们的作用机制与金属离子无关。在这里，我们研究了与肽核酸（PNA）结合物。RNA降解的速率和底物特异性与我们之前进行的DNA结合物实验中相似。尽管在某些情况下观察到聚集现象，但适当的底物识别并未受到影响。尽管我们之前合成2-氨基苯并咪唑需要HgO诱导的环化步骤，但本文描述了一种无汞的变种。