2-{2-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-5-yl]-1H-benzimidazol-6-yl}-1H-benzimidazole-6-carbonitrile | 334685-25-5

• 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-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-5-yl]-1H-benzimidazol-6-yl}-1H-benzimidazole-6-carbonitrile
• 英文别名: 2-[2-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-5-yl]-3H-benzimidazol-5-yl]-3H-benzimidazole-5-carbonitrile
• CAS: 334685-25-5
• 化学式: C₂₈H₁₈N₈O
• 分子量: 482.504
• InChiKey: XZBFCSJVTSDEJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  131.95
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-{2-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-5-yl]-1H-benzimidazol-6-yl}-1H-benzimidazole-6-carbonitrile 在 氢溴酸 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-[3-(dimethylamino)propyl]-2-{2-[2-(4-hydroxyphenyl)-1H-imidazo[4,5-b]pyridin-5-yl]-1H-benzimidazol-6-yl}-1H-benzimidazole-6-carboxamide
  参考文献：
  名称：

  Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code

  摘要：

  A series of three-ring analogs of the minor-groove-binding molecule Hoechst 33258 (1), consisting of benzimidazole (B), imidazopyridine (P), and hydroxybenzimidazole (H) monomers, have been synthesized in order to investigate both their sequence specificity and binding modes. MPE.Fe-II Footprinting has revealed the preference of both PBB and BBB ligands for 5'-WGWWW-3' and 5'-WCWWW-3' tracts, as well as A T-rich sequences. Affinity-cleavage titrations show no evidence for a 2:1 binding mode of these Hoechst analogs. Importantly, all derivatives are oriented in one direction at each of their binding sites. The implications of these results for the design of minor-groove-binding small molecules is discussed.

  DOI：

  10.1002/1522-2675(20000906)83:9<2197::aid-hlca2197>3.0.co;2-n
• 作为产物：
  描述：

  5-cyano-2-(3,4-diaminophenyl)benzimidazole 、 2-(4-Methoxy-phenyl)-3H-imidazo[4,5-b]pyridine-5-carbaldehyde 在 硝基苯 作用下， 反应 19.0h， 以51%的产率得到2-{2-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-5-yl]-1H-benzimidazol-6-yl}-1H-benzimidazole-6-carbonitrile
  参考文献：
  名称：

  Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code

  摘要：

  A series of three-ring analogs of the minor-groove-binding molecule Hoechst 33258 (1), consisting of benzimidazole (B), imidazopyridine (P), and hydroxybenzimidazole (H) monomers, have been synthesized in order to investigate both their sequence specificity and binding modes. MPE.Fe-II Footprinting has revealed the preference of both PBB and BBB ligands for 5'-WGWWW-3' and 5'-WCWWW-3' tracts, as well as A T-rich sequences. Affinity-cleavage titrations show no evidence for a 2:1 binding mode of these Hoechst analogs. Importantly, all derivatives are oriented in one direction at each of their binding sites. The implications of these results for the design of minor-groove-binding small molecules is discussed.

  DOI：

  10.1002/1522-2675(20000906)83:9<2197::aid-hlca2197>3.0.co;2-n