{1-[2'-(4-Methoxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester | 391903-26-7

• 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: {1-[2'-(4-Methoxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester
• CAS: 391903-26-7
• 化学式: C₃₀H₃₂N₆O₃
• 分子量: 524.622
• InChiKey: CHZICLRJBHZWOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108.16
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 {1-[2'-(4-Methoxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-[2'-(4-Methoxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-pyrrolidin-3-ylamine; compound with trifluoro-acetic 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 In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent.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
• 作为产物：
  描述：

  3,4-二氨基苯甲酸 在 盐酸 、 manganese(IV) oxide 、 sodium disulfite 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.0h， 生成 {1-[2'-(4-Methoxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-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