2'-(4-methoxy-phenyl)-[2,6'] bis(1H-benzoimidazole)-6-carboxylic acid | 391903-21-2

• 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'-(4-methoxy-phenyl)-[2,6'] bis(1H-benzoimidazole)-6-carboxylic acid
• 英文别名: 2-[2-(4-methoxyphenyl)-3H-benzimidazol-5-yl]-3H-benzimidazole-5-carboxylic acid
• CAS: 391903-21-2
• 化学式: C₂₂H₁₆N₄O₃
• 分子量: 384.394
• InChiKey: VZVSMENQTZSGPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  103.89
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2'-(4-methoxy-phenyl)-[2,6'] bis(1H-benzoimidazole)-6-carboxylic acid 在 吡啶 、 sodium disulfite 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 {1-[2''-(4-Methoxy-phenyl)-3H,3'H,3''H-[2,5';2',5'']terbenzoimidazol-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Tris-benzimidazole derivatives: design, synthesis and DNA sequence recognition

  摘要：

  Two tris-benzimidazole derivatives have been designed and synthesized based on the known structures of the bis-benzimidazole stain Hoechst 33258 complexed to short oligonucleotide duplexes derived from single crystal X-ray studies and from NMR. In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent. Whereas one tris-benzimidazole carries a N-methyl-piperazine at the 6-position, the other one has this group replaced by a 2-amino-pyrrolidine ring. This latter substituent results in stronger DNA binding. The optimized synthesis of the drugs is described. The two tris-benzimidazoles exhibit high AT-base pair (bp) selectivity evident in footprinting experiments which show that five to six base pairs are protected by the tris-benzimidazoles as compared to four to five protected by the bis-benzimidazoles. The tris-benzimidazoles bind well to sequences like 5-TAAAC, 5'-TTTAC and 5'-TTTAT, but it is also evident that they can bind weakly to sequences such as 5'-TATGTT-3' where the continuity of an AT stretch is interrupted by a single G-C base pair. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00170-5
• 作为产物：
  描述：

  3,4-二硝基苯甲酸 在 palladium on activated charcoal 吡啶 、 sodium disulfite 、 lithium aluminium tetrahydride 、 氯化亚砜 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 2'-(4-methoxy-phenyl)-[2,6'] bis(1H-benzoimidazole)-6-carboxylic acid
  参考文献：
  名称：

  Tris-benzimidazole derivatives: design, synthesis and DNA sequence recognition

  摘要：

  Two tris-benzimidazole derivatives have been designed and synthesized based on the known structures of the bis-benzimidazole stain Hoechst 33258 complexed to short oligonucleotide duplexes derived from single crystal X-ray studies and from NMR. In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent. Whereas one tris-benzimidazole carries a N-methyl-piperazine at the 6-position, the other one has this group replaced by a 2-amino-pyrrolidine ring. This latter substituent results in stronger DNA binding. The optimized synthesis of the drugs is described. The two tris-benzimidazoles exhibit high AT-base pair (bp) selectivity evident in footprinting experiments which show that five to six base pairs are protected by the tris-benzimidazoles as compared to four to five protected by the bis-benzimidazoles. The tris-benzimidazoles bind well to sequences like 5-TAAAC, 5'-TTTAC and 5'-TTTAT, but it is also evident that they can bind weakly to sequences such as 5'-TATGTT-3' where the continuity of an AT stretch is interrupted by a single G-C base pair. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00170-5