1-[N-(benzimidazol-2-yl)aminomethyl]-3-[N-(tert-butoxycarbonyl)aminomethyl]benzene | 848408-58-2

• 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: 1-[N-(benzimidazol-2-yl)aminomethyl]-3-[N-(tert-butoxycarbonyl)aminomethyl]benzene
• CAS: 848408-58-2
• 化学式: C₂₀H₂₄N₄O₂
• 分子量: 352.436
• InChiKey: OKJSZRSUHLOTEN-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.04
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[N-(benzimidazol-2-yl)aminomethyl]-3-[N-(tert-butoxycarbonyl)aminomethyl]benzene 在 盐酸 作用下， 以 甲醇 为溶剂， 生成
  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：

  1-[N'-(2-aminophenyl)thioureidomethyl]-3-[N-(tert-butoxycarbonyl)aminomethyl]benzene 在 sulfur 、 mercury(II) oxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以94%的产率得到1-[N-(benzimidazol-2-yl)aminomethyl]-3-[N-(tert-butoxycarbonyl)aminomethyl]benzene
  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