N-{3-[(3-Amino-propyl)-methyl-amino]-propyl}-2-{4-[2'-(4-hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetamide | 416850-41-4

• 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: N-{3-[(3-Amino-propyl)-methyl-amino]-propyl}-2-{4-[2'-(4-hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetamide
• CAS: 416850-41-4
• 化学式: C₃₃H₄₁N₉O₂
• 分子量: 595.748
• InChiKey: PLBJLPUOADJZAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  142.43
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-[2-(3-Hydroxy-5-oxo-morpholin-4-yl)-ethyl]-morpholine-2,6-dione 、 N-{3-[(3-Amino-propyl)-methyl-amino]-propyl}-2-{4-[2'-(4-hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetamide 在 N-甲基吡咯烷酮 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.42h， 以0.5 mg的产率得到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：

  2-硝基-5-氯苯胺 在 palladium on activated charcoal 氢溴酸 、 氢气 、 potassium carbonate 、 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 水 、 乙酸乙酯 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 N-{3-[(3-Amino-propyl)-methyl-amino]-propyl}-2-{4-[2'-(4-hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetamide
  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