4-amino-3-(3-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethyl}thioureido)benzoic acid methyl ester | 848408-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-3-(3-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethyl}thioureido)benzoic acid methyl ester
• CAS: 848408-62-8
• 化学式: C₂₅H₄₂N₆O₆S
• 分子量: 554.711
• InChiKey: PMEIVNWWJDNZSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  156.28
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-amino-3-(3-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethyl}thioureido)benzoic acid methyl ester 在 sulfur 、 mercury(II) oxide 作用下， 以 乙醇 为溶剂， 以97%的产率得到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
• 作为产物：
  描述：

  三(2-氨基乙基)胺 在 咪唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 49.5h， 生成 4-amino-3-(3-{2-[bis-(2-{tert-butoxycarbonylamino}ethyl)amino]ethyl}thioureido)benzoic acid methyl ester
  参考文献：
  名称：

  Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole)

  摘要：

  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。

  DOI：

  10.3762/bjoc.11.55