N,N'-bis(3-(1-thyminylpropyl))-4,13-diaza-18-crown-6 | 116393-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N,N'-bis(3-(1-thyminylpropyl))-4,13-diaza-18-crown-6
• 英文别名: N,N'-bis-<3-(thymin-1-yl)propyl>-4,13-diaza-18-crown-6；N,N'-bis<3-(1-thyminyl)propyl>-4,13-diaza-18-crown-6；5-methyl-1-[3-[16-[3-(5-methyl-2,4-dioxopyrimidin-1-yl)propyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propyl]pyrimidine-2,4-dione
• CAS: 116393-01-2
• 化学式: C₂₈H₄₆N₆O₈
• 分子量: 594.709
• InChiKey: GXTNPAFJCOCCOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  153.12
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  胸腺嘧啶 在 四甲基氢氧化铵 、 六甲基二硅氮烷 作用下， 反应 240.0h， 生成 N,N'-bis(3-(1-thyminylpropyl))-4,13-diaza-18-crown-6
  参考文献：
  名称：

  一种分子盒，基于具有腺嘌呤和胸腺嘧啶侧臂的双臂套索状醚，可在水中自组装

  摘要：

  已经制备了两个4,13-二氮杂-18-冠-6衍生物，其中侧臂终止于腺嘌呤或胸腺嘧啶残基。分子量测定表明它们在水中缔合，并在同一溶剂中与十二烷-1,12-二铵盐形成三元络合物，可能涉及DNA型相互作用和总共十个氢键。

  DOI：

  10.1039/c39870001686

文献信息

• ——
  作者：Stephen L. De Wall、Leonard J. Barbour、Otto F. Schall、George W. Gokel

  DOI：10.1023/a:1009534904760

  日期：——
• Molecular Boxes Derived from Crown Ethers and Nucleotide Bases: Probes for Hoogsteen vs Watson-Crick H-Bonding and Other Base-Base Interactions in Self-Assembly Processes
  作者：Otto F. Schall、George W. Gokel

  DOI：10.1021/ja00093a005

  日期：1994.7

  Bibracchial lariat ethers based upon 4, 13-diaza-18-crown-6 having -(CH2)(3)-sidearms terminated in adenine or thymine have been prepared and characterized. The three structures are as follows: adenine-(CH2)(3)-(N18N)(CH2)(3)-adenine (A-O-A), thymine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (T-O-T), and adenine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (A-O-T). Association of the nucleotide bases was expected to afford molecular boxes or other aggregates that would be stabilized by interactions between or among the nucleotide bases. These compounds have been studied in solution by H-1-NMR spectroscopy and by vapor pressure osmometry to determine the extent of association as well as what interactions occur between the bases. The H-1-NMR solution studies involved both temperature and concentration dependence and NOE studies. Several lines of evidence make clear that association does occur in CDCl3 with an association constant for A-O-A with T-O-T of 855 M(-1). Both intra- and intermolecular H-bonding interactions are detected. Hoogsteen binding modes appear to play a very important role in these flexible systems. The A-O-A.T-O-T box may also comprise a ditopic receptor system in which the sides of the box are Ade::Thy pairs and the ends are crown ethers. We have studied such systems in the presence of decanediyldiammonium and dodecanediyldiammonium salts and report evidence for a ternary induced-fit receptor complex.
• KIM, MINSOOK;GOKEL, GEORGE W., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 22, 1686-1688
  作者：KIM, MINSOOK、GOKEL, GEORGE W.

  DOI：——

  日期：——