N,N'-bis<3-2-(2-adenin-9-ylethyl)thymin-1-yl>propyl>-4,13-diaza-18-crown-6 | 142952-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N,N'-bis<3-2-(2-adenin-9-ylethyl)thymin-1-yl>propyl>-4,13-diaza-18-crown-6
• 英文别名: 2-[2-(6-Aminopurin-9-yl)ethoxy]-1-[3-[16-[3-[2-[2-(6-aminopurin-9-yl)ethoxy]-5-methyl-4-oxopyrimidin-1-yl]propyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propyl]-5-methylpyrimidin-4-one
• CAS: 142952-63-4
• 化学式: C₄₂H₆₀N₁₆O₈
• 分子量: 917.041
• InChiKey: SOYXBUQFFZYRAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  66
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  266
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  9-(2-氯-乙基)-9H-嘌呤-6-基胺 、 N,N'-bis(3-(1-thyminylpropyl))-4,13-diaza-18-crown-6 在 sodium carbonate 、 sodium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以85%的产率得到N,N'-bis<3-2-(2-adenin-9-ylethyl)thymin-1-yl>propyl>-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Hydrogen Bonding and π-Stacking Interactions as Organizing Elements in Lariat Ethers Containing Nucleotide Bases

  摘要：

  Two new bibracchial lariat ethers have been prepared as flexible model systems for nucleotide H-bonding and pi-stacking interactions. In both compounds, nucleotide bases terminate side arms attached at the nitrogen atoms of a diaza-18-crown-6 macroring. Each side arm is terminated by one or more nucleotide bases. The unsymmetrical structure is ade-CH2CH2CH2CH2CH2-thy-CH2CH2-ade (A-O-T-A). The symmetrical compound is ade-CH2CH2-thy-CH2CH2CH2CH2CH2CH2-thy-CH2CH2-ade (A-T-O-T-A). NMR studies show that the thy-ade side arm organizes by pi-stacking in both A-O-T-A and A-T-O-T-A. Both compounds exhibit hydrogen bonding between the stacked base pair and the opposite adenine. A-O-T-A exhibits a stronger interaction resulting from the enforced interplay of noncovalent forces, as evidenced by one- and two-dimensional NMR experiments. This compound also presented the opportunity to detect and examine single hydrogen-bonded interactions between two adenine bases. The effects of conformational rigidity, side arm orientation, metal ion complexation, and variations in solvent were assessed for both compounds. The results presented here indicate that an increase in the medium's dielectric constant or complexation of metal cations appear to modulate the interplay between hydrogen bonding and stacking interactions.

  DOI：

  10.1021/jo951959l

文献信息

• Hydrogen Bonding and π-Stacking Interactions as Organizing Elements in Lariat Ethers Containing Nucleotide Bases
  作者：Otto F. Schall、George W. Gokel

  DOI：10.1021/jo951959l

  日期：1996.1.1

  Two new bibracchial lariat ethers have been prepared as flexible model systems for nucleotide H-bonding and pi-stacking interactions. In both compounds, nucleotide bases terminate side arms attached at the nitrogen atoms of a diaza-18-crown-6 macroring. Each side arm is terminated by one or more nucleotide bases. The unsymmetrical structure is ade-CH2CH2CH2CH2CH2-thy-CH2CH2-ade (A-O-T-A). The symmetrical compound is ade-CH2CH2-thy-CH2CH2CH2CH2CH2CH2-thy-CH2CH2-ade (A-T-O-T-A). NMR studies show that the thy-ade side arm organizes by pi-stacking in both A-O-T-A and A-T-O-T-A. Both compounds exhibit hydrogen bonding between the stacked base pair and the opposite adenine. A-O-T-A exhibits a stronger interaction resulting from the enforced interplay of noncovalent forces, as evidenced by one- and two-dimensional NMR experiments. This compound also presented the opportunity to detect and examine single hydrogen-bonded interactions between two adenine bases. The effects of conformational rigidity, side arm orientation, metal ion complexation, and variations in solvent were assessed for both compounds. The results presented here indicate that an increase in the medium's dielectric constant or complexation of metal cations appear to modulate the interplay between hydrogen bonding and stacking interactions.