1,11-bis-[2,2'-(5-phenoxy-1,3-phenylene)-bis[5-(4-methyl-1-pi-perazinyl)-1H-benzimidazole]]-3,6,9-trioxo-undecane | 1370287-57-2

• 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: 1,11-bis-[2,2'-(5-phenoxy-1,3-phenylene)-bis[5-(4-methyl-1-pi-perazinyl)-1H-benzimidazole]]-3,6,9-trioxo-undecane
• 英文别名: 2-[3-[2-[2-[2-[2-[3,5-bis[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]-5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenyl]-6-(4-methylpiperazin-1-yl)-1H-benzimidazole
• CAS: 1370287-57-2
• 化学式: C₆₈H₈₂N₁₆O₅
• 分子量: 1203.5
• InChiKey: BTQGSWNVGYMULP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  89
• 可旋转键数：
  22
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  187
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  1,11-bis-[phenoxy-(3,5-dicarbaldehyde)]-3,6,9-trioxo undecane 、 4-(4-甲基哌嗪基)-1,2-苯二胺 在 sodium metabisulfite 作用下， 以 水 为溶剂， 反应 8.0h， 以61%的产率得到1,11-bis-[2,2'-(5-phenoxy-1,3-phenylene)-bis[5-(4-methyl-1-pi-perazinyl)-1H-benzimidazole]]-3,6,9-trioxo-undecane
  参考文献：
  名称：

  Dimeric 1,3-Phenylene-bis(piperazinyl benzimidazole)s: Synthesis and Structure–Activity Investigations on their Binding with Human Telomeric G-Quadruplex DNA and Telomerase Inhibition Properties

  摘要：

  Ligand-induced stabilization of G-quadruplex structures formed by the human telomeric DNA is an active area of research. The compounds which stabilize the G-quadruplexes often lead to telomerase inhibition. Herein we present the results of interaction of new monomeric and dimeric ligands having 1,3-phenylene-bis(piperazinyl benzimidazole) unit with G-quadruplex DNA (G4DNA) formed by human telomeric repeat d[(G(3)T(2)A)(3)G(3)]. These ligands efficiently stabilize the preformed G4DNA in the presence of 100 mM monovalent alkali metal ions. Also, the G4DNA formed in the presence of low concentrations of ligands in 100 mM K+ adopts a highly stable parallel-stranded conformation. The G-quadruplexes formed in the presence of the dimeric compound are more stable than that induced by the corresponding monomeric counterpart. The dimeric ligands having oligo-oxyethylene spacers provide much higher stability to the preformed G4DNA and also exert significantly higher telomerase inhibition activity. Computational aspects have also been discussed.

  DOI：

  10.1021/jm200860b

文献信息

• Dimeric 1,3-Phenylene-bis(piperazinyl benzimidazole)s: Synthesis and Structure–Activity Investigations on their Binding with Human Telomeric G-Quadruplex DNA and Telomerase Inhibition Properties
  作者：Akash K Jain、Ananya Paul、Basudeb Maji、K. Muniyappa、Santanu Bhattacharya

  DOI：10.1021/jm200860b

  日期：2012.4.12

  Ligand-induced stabilization of G-quadruplex structures formed by the human telomeric DNA is an active area of research. The compounds which stabilize the G-quadruplexes often lead to telomerase inhibition. Herein we present the results of interaction of new monomeric and dimeric ligands having 1,3-phenylene-bis(piperazinyl benzimidazole) unit with G-quadruplex DNA (G4DNA) formed by human telomeric repeat d[(G(3)T(2)A)(3)G(3)]. These ligands efficiently stabilize the preformed G4DNA in the presence of 100 mM monovalent alkali metal ions. Also, the G4DNA formed in the presence of low concentrations of ligands in 100 mM K+ adopts a highly stable parallel-stranded conformation. The G-quadruplexes formed in the presence of the dimeric compound are more stable than that induced by the corresponding monomeric counterpart. The dimeric ligands having oligo-oxyethylene spacers provide much higher stability to the preformed G4DNA and also exert significantly higher telomerase inhibition activity. Computational aspects have also been discussed.