{4-[2'-(4-Hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetic acid | 188247-21-4

• 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: {4-[2'-(4-Hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetic acid
• CAS: 188247-21-4
• 化学式: C₂₆H₂₄N₆O₃
• 分子量: 468.515
• InChiKey: XMBYLODBAXYYLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121.37
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {4-[2'-(4-Hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetic acid 在 N-甲基吡咯烷酮 、 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 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.42h， 生成 2-((carboxymethyl){2-[(carbxymethyl)({N-[3-({3-[2-(4-{2-[2-(4-hydroxyphenyl)-1H-benzomidazol-6-yl]-1H-benzimidazol-6-yl}-piperazin-1-yl)acetylamino]propyl}methylamino)propyl]carbamoyl}methyl)amino]ethyl}amino)acetic 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：

  ethyl 2-(4-{2-[2-(4-methoxyphenyl)-1H-benzimidazol-6-yl]-1H-benzimidazol-6-yl}piperazin-1-yl)acetate 在 氢溴酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 {4-[2'-(4-Hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetic 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

文献信息

• Radioprotectors
  申请人：Peter MacCallum Cancer Institute

  公开号：EP2044938B1

  公开（公告）日：2015-02-18