1,1'-[1,4-phenylenebis(methylene)]bis(4-piperazinecarbaldehyde) | 155791-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1'-[1,4-phenylenebis(methylene)]bis(4-piperazinecarbaldehyde)
• 英文别名: 4-[[4-[(4-Formylpiperazin-1-yl)methyl]phenyl]methyl]piperazine-1-carbaldehyde
• CAS: 155791-74-5
• 化学式: C₁₈H₂₆N₄O₂
• 分子量: 330.43
• InChiKey: SKSIPYOKPXHGAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-[1,4-phenylenebis(methylene)]bis(4-piperazinecarbaldehyde) 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以78%的产率得到1,1'-[1,4-phenylenebis(methylene)]bispiperazine
  参考文献：
  名称：

  Syntheses and DNA photocleavage by mono- and bis-phenothiazinium–piperazinexylene intercalators

  摘要：

  Chromophore systems consisting of one (compound 5) or two (compound 6) phenothiazine rings covalently attached to a bis-piperazinexylene chain were synthesized and evaluated as DNA photocleaving agents. In the presence of DNA, the compounds were shown to monointercalate in their deaggregated forms and to strongly absorb red wavelengths of light. Reactions containing micromolar concentrations of compound produced robust photocleavage of plasmid DNA under near-physiological conditions of temperature and pH (22 degrees C and pH 7.0). Phenothiazines 5 and 6 increased the T-m of calf thymus DNA by 17 and 19 degrees C, indicating that significant levels of duplex stabilization were produced. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.105
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 1-甲醛哌嗪 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到1,1'-[1,4-phenylenebis(methylene)]bis(4-piperazinecarbaldehyde)
  参考文献：
  名称：

  Syntheses and DNA photocleavage by mono- and bis-phenothiazinium–piperazinexylene intercalators

  摘要：

  Chromophore systems consisting of one (compound 5) or two (compound 6) phenothiazine rings covalently attached to a bis-piperazinexylene chain were synthesized and evaluated as DNA photocleaving agents. In the presence of DNA, the compounds were shown to monointercalate in their deaggregated forms and to strongly absorb red wavelengths of light. Reactions containing micromolar concentrations of compound produced robust photocleavage of plasmid DNA under near-physiological conditions of temperature and pH (22 degrees C and pH 7.0). Phenothiazines 5 and 6 increased the T-m of calf thymus DNA by 17 and 19 degrees C, indicating that significant levels of duplex stabilization were produced. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.105

文献信息

• Design and Synthesis of RNA-Specific Groove-Binding Cations: Implications for Antiviral Drug Design
  作者：Adrian W. McConnaughie、Jaroslaw Spychala、Min Zhao、David Boykin、W. David Wilson

  DOI：10.1021/jm00034a004

  日期：1994.4

  As as initial step in the design of structure-specific RNA-interactive molecules as potential antiviral agents, we have focused on the synthesis of molecules that exhibit strong and preferential binding to duplex RNA. A series of polycationic ligands have been synthesized, and the degree of preferential binding to RNA has initially been determined by thermal denaturation (Delta T-m) with both RNA [poly(A) poly(U)] and DNA [poly(dA).poly(dT)] polymers at a variety of pH values. Seven compounds from the series exhibit a substantial degree of RNA-selective binding. The relatively high Delta T-m values obtained suggest a specific mode of interaction between these ligands and the RNA helix. By contrast, the much lower Delta T-m values with poly(dA) poly(dT) DNA reflect a more nonspecific interaction mode, A viscometric titration study with poly(A) poly(U) confirms that they do not bind by intercalation. The results, combined with the known structure and electronegative potential of duplex RNA, suggest that these molecules bind in the major groove via specific electrostatic and/or hydrogen-bonded interactions.
• Syntheses and DNA photocleavage by mono- and bis-phenothiazinium–piperazinexylene intercalators
  作者：Beth Wilson、María-José Fernández、Antonio Lorente、Kathryn B. Grant

  DOI：10.1016/j.tet.2008.01.105

  日期：2008.4

  Chromophore systems consisting of one (compound 5) or two (compound 6) phenothiazine rings covalently attached to a bis-piperazinexylene chain were synthesized and evaluated as DNA photocleaving agents. In the presence of DNA, the compounds were shown to monointercalate in their deaggregated forms and to strongly absorb red wavelengths of light. Reactions containing micromolar concentrations of compound produced robust photocleavage of plasmid DNA under near-physiological conditions of temperature and pH (22 degrees C and pH 7.0). Phenothiazines 5 and 6 increased the T-m of calf thymus DNA by 17 and 19 degrees C, indicating that significant levels of duplex stabilization were produced. (c) 2008 Elsevier Ltd. All rights reserved.