1,1'-(1,3-propanediyl)bis(4-cyanopiperidine)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,1'-(1,3-propanediyl)bis(4-cyanopiperidine)
• 英文别名: 1-[3-(4-Cyano-1-piperidyl)propyl]piperidine-4-carbonitrile；1-[3-(4-cyanopiperidin-1-yl)propyl]piperidine-4-carbonitrile
• 化学式: C₁₅H₂₄N₄
• 分子量: 260.382
• InChiKey: UDRBMONVVHHKBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-diaminoethane dihydrochloride 、 乙二胺 、 1,1'-(1,3-propanediyl)bis(4-cyanopiperidine) 反应 6.0h， 以38%的产率得到1,1'-(1,3-propanediyl)bis(4-imidazolinylpiperidine) tetrahydrochloride
  参考文献：
  名称：

  Design and Synthesis of RNA-Specific Groove-Binding Cations: Implications for Antiviral Drug Design

  摘要：

  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.

  DOI：

  10.1021/jm00034a004
• 作为产物：
  描述：

  4-氰基哌啶 、 1,3-二溴丙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 3.5h， 以75%的产率得到1,1'-(1,3-propanediyl)bis(4-cyanopiperidine)
  参考文献：
  名称：

  Design and Synthesis of RNA-Specific Groove-Binding Cations: Implications for Antiviral Drug Design

  摘要：

  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.

  DOI：

  10.1021/jm00034a004

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.