2-<2-(4-aminophenyl)-6-benzimidazoyl>-6-(1-methyl-4-piperazinyl)benzimidazole | 23476-82-6

• 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-<2-(4-aminophenyl)-6-benzimidazoyl>-6-(1-methyl-4-piperazinyl)benzimidazole
• 英文别名: 4-[5-(4-methyl-piperazin-1-yl)-1(3)H,1'(3')H-[2,5']bibenzoimidazolyl-2'-yl]-aniline；4-[6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]aniline
• CAS: 23476-82-6
• 化学式: C₂₅H₂₅N₇
• 分子量: 423.52
• InChiKey: IWAVVJLAHUMPAM-UHFFFAOYSA-N

物化性质

• 沸点：
  749.4±70.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.86
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-<2-(4-aminophenyl)-6-benzimidazoyl>-6-(1-methyl-4-piperazinyl)benzimidazole 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 以94 %的产率得到
  参考文献：
  名称：

  跟踪和记录细胞器中细胞内氧浓度的变化：叠氮化物修饰荧光探针的制备和功能。

  摘要：

  追踪缺氧环境和氧水平的变化有助于阐明病理机制。在这项研究中，我们尝试设计可以在缺氧条件下被激活以显示荧光并且可以移动到特定细胞器的分子探针。考虑到叠氮基团在缺氧条件下会被还原酶选择性还原为伯胺，我们制备了Hoechst和带有叠氮基团的荧光团Cy-5衍生物（Hoechst-N3和Cy-N3）作为缺氧探针。 Hoechst-N3和Cy-N3显示出微弱的荧光，但一旦在缺氧细胞的胞浆中被激活，它们就会显示出强烈的荧光，然后移动到它们的目标细胞器、细胞核和线粒体。此外，当这些探针以正确的顺序施用于细胞时，每个探针都会响应当时细胞内的氧浓度而被激活，并在目标细胞器处表现出氧浓度依赖性荧光。通过测量细胞核和线粒体的荧光强度，我们成功追踪了细胞内氧水平的变化历史。因此，我们实现了细胞内氧气状态的跟踪和记录。

  DOI：

  10.1039/d4ra01625d
• 作为产物：
  描述：

  2-(3,4-diaminophenyl)-6-(1-methyl-4-piperazinyl)benzimidazole 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2-<2-(4-aminophenyl)-6-benzimidazoyl>-6-(1-methyl-4-piperazinyl)benzimidazole
  参考文献：
  名称：

  DNA-Tethered Hoechst Groove-Binding Agents:  Duplex Stabilization and Fluorescence Characteristics

  摘要：

  Fluorescent Hoechst 33258 analogues have been synthesized in which the terminal phenol moiety is employed as a site for the introduction of a linker to permit covalent attachment of the fluorophores to oligo(deoxynucleotides). Hybridization by the DNA-Hoechst conjugates to target sequences generates the DNA minor groove structure and triggers a binding event by the tethered Hoechst agent. The attendant fluorescence signal reports upon this hybridization event. Conjugation of the Hoechst derivatives to the DNA sequences employs a cystamine linker tethered to an internucleotide phosphorus residue. This mode of conjugation maximizes the versatility of linker placement and minimizes the associated chemistry required to introduce the linker. Two related Hoechst derivatives have been synthesized; both contain a bromoacetamido linker for conjugation to the oligonucleotides. With each Hoechst derivative, two pairs of diastereomeric (R(p) and S-p) oligo(deoxynucleotide) conjugates were prepared to provide the tethered Hoechst groove binders with two different orientations within the dA-dT rich minor groove. T-m measurements suggest that while all of the conjugates provide some increased duplex stability, the diastereomeric conjugates tentatively assigned the R(p) configuration exhibit nearly 20 degrees C increases in T-m values for the double-stranded dodecameric complexes, while those tentatively assigned as the S-p diastereomers exhibit only moderate 4-8 degrees C increases in T-m values. The fluorescence characteristics of the conjugates are more variable, with one complex exhibiting a 23-fold enhancement in quantum yield effects, very similar to that observed for a free untethered Hoechst 33258 fluorophore bound to duplex DNA.

  DOI：

  10.1021/ja960948m