2-[2-(4-chloro-7-methoxy-2-methyl-1H-benzimidazol-6-yl)-1H-benzimidazol-6-yl]-1H-benzimidazole-6-carbonitrile | 334685-27-7

• 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-(4-chloro-7-methoxy-2-methyl-1H-benzimidazol-6-yl)-1H-benzimidazol-6-yl]-1H-benzimidazole-6-carbonitrile
• 英文别名: 2-[2-(7-chloro-4-methoxy-2-methyl-3H-benzimidazol-5-yl)-3H-benzimidazol-5-yl]-3H-benzimidazole-5-carbonitrile
• CAS: 334685-27-7
• 化学式: C₂₄H₁₆ClN₇O
• 分子量: 453.89
• InChiKey: GDXYQNMJVJGCKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-(4-chloro-7-methoxy-2-methyl-1H-benzimidazol-6-yl)-1H-benzimidazol-6-yl]-1H-benzimidazole-6-carbonitrile 在 氢溴酸 作用下， 反应 0.5h， 生成 7''-Chloro-4''-methoxy-2''-methyl-3H,3'H,3''H-[2,5';2',5'']terbenzoimidazole-5-carboxylic acid
  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：

  4-乙酰氨基-5-氯-2-甲氧基-3-硝基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 MnNO₂ 、 铁粉 、 硝基苯 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 生成 2-[2-(4-chloro-7-methoxy-2-methyl-1H-benzimidazol-6-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

文献信息

• MINOR GROOVE BINDER PHOSPHORAMIDITES AND METHODS OF USE
  申请人：Vorobiev Alexei

  公开号：US20130030166A1

  公开（公告）日：2013-01-31

  Minor groove binder phosphoramidites having unique structures have been synthesized according to particular methods. These minor groove binder phosphoramidites are useful in the preparation of oligonucleotide conjugates, particularly those for use as probes and primers.

  根据特定方法合成了具有独特结构的小沟结合剂磷酰胺酰胺。这些小沟结合剂磷酰胺酰胺在制备寡核苷酸共轭物中很有用，特别是用作探针和引物的情况。
• US9056887B2
  申请人：——

  公开号：US9056887B2

  公开（公告）日：2015-06-16
• Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code
  作者：Thomas G. Minehan、Konstanze Gottwald、Peter B. Dervan

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

  日期：2000.9.6

  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.