5-methoxy-2-[2'-(benzimidazol-5''-yl)benzimidazole-5'-yl]benzimidazole | 205749-95-7

• 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: 5-methoxy-2-[2'-(benzimidazol-5''-yl)benzimidazole-5'-yl]benzimidazole
• 英文别名: 2-(3H-benzimidazol-5-yl)-6-(6-methoxy-1H-benzimidazol-2-yl)-1H-benzimidazole
• CAS: 205749-95-7
• 化学式: C₂₂H₁₆N₆O
• 分子量: 380.409
• InChiKey: YAXLAJPQEJFOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  95.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-[2'-(benzimidazol-5''-yl)benzimidazole-5'-yl]benzimidazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到5-hydroxy-2-[2'-(benzimidazol-5''-yl)benzimidazole-5'-yl]benzimidazole
  参考文献：
  名称：

  Quantitative structure–activity relationships on 5-substituted terbenzimidazoles as topoisomerase I poisons and antitumor agents

  摘要：

  Several 5-substituted terbenzimidazoles were synthesized and evaluated as mammalian topoisomerase I poisons and for cytotoxicity against a human lymphoblastoma cell line, RPMI-8402. No correlation was observed between topoisomerase I poisoning activity and the Hansch pi value or the sigma(meta) and sigma(para) values associated with each substituent. These data suggest that electronic effects and relative lipophilicity of substituents at the 5-position of these terbenzimidazoles do not have a significant effect upon intrinsic topoisomerase I poisoning activity. There was, however, a good correlation between the relative pi values for the various subtituents evaluated and cytotoxic activity. Experimentally determined log P values did not correlate well with either cytotoxicity or pi values. Capacity factors (log k') as determined by high pressure liquid chromatography did correlate well with the it values of varied substituents and cytotoxicity. These data indicate that the relative lipophilic activity of substituents at the 5-position of these terbenzimidazoles can strongly influence relative cytotoxic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10021-9
• 作为产物：
  描述：

  2-硝基-4-甲氧基苯胺 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 硝基苯 为溶剂， 反应 3.0h， 生成 5-methoxy-2-[2'-(benzimidazol-5''-yl)benzimidazole-5'-yl]benzimidazole
  参考文献：
  名称：

  Quantitative structure–activity relationships on 5-substituted terbenzimidazoles as topoisomerase I poisons and antitumor agents

  摘要：

  Several 5-substituted terbenzimidazoles were synthesized and evaluated as mammalian topoisomerase I poisons and for cytotoxicity against a human lymphoblastoma cell line, RPMI-8402. No correlation was observed between topoisomerase I poisoning activity and the Hansch pi value or the sigma(meta) and sigma(para) values associated with each substituent. These data suggest that electronic effects and relative lipophilicity of substituents at the 5-position of these terbenzimidazoles do not have a significant effect upon intrinsic topoisomerase I poisoning activity. There was, however, a good correlation between the relative pi values for the various subtituents evaluated and cytotoxic activity. Experimentally determined log P values did not correlate well with either cytotoxicity or pi values. Capacity factors (log k') as determined by high pressure liquid chromatography did correlate well with the it values of varied substituents and cytotoxicity. These data indicate that the relative lipophilic activity of substituents at the 5-position of these terbenzimidazoles can strongly influence relative cytotoxic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10021-9

文献信息

• MINOR GROOVE BINDER PHOSPHORAMIDITES AND METHODS OF USE
  申请人：Vorobiev Alexei

  公开号：US20130030166A1

  公开（公告）日：2013-01-31

  Minor groove binder phosphoramidites having unique structures have been synthesized according to particular methods. These minor groove binder phosphoramidites are useful in the preparation of oligonucleotide conjugates, particularly those for use as probes and primers.

  根据特定方法合成了具有独特结构的小沟结合剂磷酰胺酰胺。这些小沟结合剂磷酰胺酰胺在制备寡核苷酸共轭物中很有用，特别是用作探针和引物的情况。
• US9056887B2
  申请人：——

  公开号：US9056887B2

  公开（公告）日：2015-06-16
• Quantitative structure–activity relationships on 5-substituted terbenzimidazoles as topoisomerase I poisons and antitumor agents
  作者：Jung Sun Kim、Qun Sun、Chiang Yu、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/s0968-0896(97)10021-9

  日期：1998.2

  Several 5-substituted terbenzimidazoles were synthesized and evaluated as mammalian topoisomerase I poisons and for cytotoxicity against a human lymphoblastoma cell line, RPMI-8402. No correlation was observed between topoisomerase I poisoning activity and the Hansch pi value or the sigma(meta) and sigma(para) values associated with each substituent. These data suggest that electronic effects and relative lipophilicity of substituents at the 5-position of these terbenzimidazoles do not have a significant effect upon intrinsic topoisomerase I poisoning activity. There was, however, a good correlation between the relative pi values for the various subtituents evaluated and cytotoxic activity. Experimentally determined log P values did not correlate well with either cytotoxicity or pi values. Capacity factors (log k') as determined by high pressure liquid chromatography did correlate well with the it values of varied substituents and cytotoxicity. These data indicate that the relative lipophilic activity of substituents at the 5-position of these terbenzimidazoles can strongly influence relative cytotoxic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.