赫斯特33258ANALOG3 | 23554-98-5

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 赫斯特33258ANALOG3
• 英文名称: 2'-p-tolyl-5-(4-methylpiperazinyl)-2,5'-bi-1H-benzimidazole
• 英文别名: 2'-(4-hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole；Hoechst 33258；5-(4-methyl-piperazin-1-yl)-2'-p-tolyl-1H,1'H-[2,5']bibenzoimidazolyl；2-(4-methylphenyl)-6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazole
• CAS: 23554-98-5
• 化学式: C₂₆H₂₆N₆
• 分子量: 422.533
• InChiKey: SISCTNULNFGYKU-UHFFFAOYSA-N

物化性质

• 溶解度：
  25℃：DMSO或水 避光

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

生物活性方面，Hoechst 33258 类似物 3 是一种与 Hoechst 染料类似的物质，能够结合 DNA 并发出蓝色荧光。

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲腈 在 aluminum nickel 甲酸 作用下， 以 硝基苯 为溶剂， 反应 6.0h， 生成 赫斯特33258ANALOG3
  参考文献：
  名称：

  Substituted 2,5‘-Bi-1H-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity

  摘要：

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.

  DOI：

  10.1021/jm950412w

文献信息

• COUNTERSTAINS FOR A BIOLOGICAL SAMPLE
  申请人：KEY MARC

  公开号：US20170299482A1

  公开（公告）日：2017-10-19

  The present disclosure relates to counterstains for staining a biological sample on a single slide in preparation for microscopic examination. The counterstains are used to analyze the sample on the single slide using both brightfield and fluorescent illumination. The counterstains can identify both morphological details and molecular structures within the cells contained in the sample. The counterstains can be used in conjunction with other molecular stains.
• Substituted 2,5‘-Bi-1<i>H</i>-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity
  作者：Jung Sun Kim、Barbara Gatto、Chiang Yu、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1021/jm950412w

  日期：1996.1.1

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.