4-(N-tert-butoxycarbonylamino)-N-{4-[N',N''-di(tert-butoxycarbonyl)-2-aminoimidazolino]phenyl}benzamide | 1374578-56-9

• 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-(N-tert-butoxycarbonylamino)-N-{4-[N',N''-di(tert-butoxycarbonyl)-2-aminoimidazolino]phenyl}benzamide
• 英文别名: Ditert-butyl 2-[4-[[4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]amino]phenyl]iminoimidazolidine-1,3-dicarboxylate
• CAS: 1374578-56-9
• 化学式: C₃₁H₄₁N₅O₇
• 分子量: 595.696
• InChiKey: FUKHLBRQKHGWNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(N-tert-butoxycarbonylamino)-N-{4-[N',N''-di(tert-butoxycarbonyl)-2-aminoimidazolino]phenyl}benzamide 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 27.0h， 以92%的产率得到4-amino-N-[4-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]benzamide;hydrochloride
  参考文献：
  名称：

  High DNA Affinity of a Series of Peptide Linked Diaromatic Guanidinium-like Derivatives

  摘要：

  In this paper we report the design and synthesis of a new family of asymmetric peptide linked diaromatic dications as potent DNA minor groove binders. These peptide-linked compounds, with a linear core, displayed a much larger affinity than other guanidinium-like derivatives from the same series with curved cores. As a first screening, the DNA affinity of these structures was evaluated by means of thermal denaturation experiments, finding that the nature of the cation (guanidinium vs 2-aminoimidazolinium) significantly influenced the binding strength. Their binding affinity was assessed by implementing further biophysical measurements such as surface plasmon resonance and circular dichroism. In particular, it was observed that compounds 6, 7, and 8 displayed both a strong binding affinity and significant selectivity for AT oligonucleotides. In addition, the thermodynamics of their binding was evaluated using isothermal titration calorimetry, indicating that the binding is derived from favorable enthalpic and entropic contributions.

  DOI：

  10.1021/jm300296f
• 作为产物：
  描述：

  tert-butyl (4-((4-aminophenyl)carbamoyl)phenyl)carbamate 、 2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到4-(N-tert-butoxycarbonylamino)-N-{4-[N',N''-di(tert-butoxycarbonyl)-2-aminoimidazolino]phenyl}benzamide
  参考文献：
  名称：

  High DNA Affinity of a Series of Peptide Linked Diaromatic Guanidinium-like Derivatives

  摘要：

  In this paper we report the design and synthesis of a new family of asymmetric peptide linked diaromatic dications as potent DNA minor groove binders. These peptide-linked compounds, with a linear core, displayed a much larger affinity than other guanidinium-like derivatives from the same series with curved cores. As a first screening, the DNA affinity of these structures was evaluated by means of thermal denaturation experiments, finding that the nature of the cation (guanidinium vs 2-aminoimidazolinium) significantly influenced the binding strength. Their binding affinity was assessed by implementing further biophysical measurements such as surface plasmon resonance and circular dichroism. In particular, it was observed that compounds 6, 7, and 8 displayed both a strong binding affinity and significant selectivity for AT oligonucleotides. In addition, the thermodynamics of their binding was evaluated using isothermal titration calorimetry, indicating that the binding is derived from favorable enthalpic and entropic contributions.

  DOI：

  10.1021/jm300296f

文献信息

• High DNA Affinity of a Series of Peptide Linked Diaromatic Guanidinium-like Derivatives
  作者：Padraic S. Nagle、Fernando Rodriguez、Binh Nguyen、W. David Wilson、Isabel Rozas

  DOI：10.1021/jm300296f

  日期：2012.5.10

  In this paper we report the design and synthesis of a new family of asymmetric peptide linked diaromatic dications as potent DNA minor groove binders. These peptide-linked compounds, with a linear core, displayed a much larger affinity than other guanidinium-like derivatives from the same series with curved cores. As a first screening, the DNA affinity of these structures was evaluated by means of thermal denaturation experiments, finding that the nature of the cation (guanidinium vs 2-aminoimidazolinium) significantly influenced the binding strength. Their binding affinity was assessed by implementing further biophysical measurements such as surface plasmon resonance and circular dichroism. In particular, it was observed that compounds 6, 7, and 8 displayed both a strong binding affinity and significant selectivity for AT oligonucleotides. In addition, the thermodynamics of their binding was evaluated using isothermal titration calorimetry, indicating that the binding is derived from favorable enthalpic and entropic contributions.