1-benzyl-7-methyl-5'-O-(4-methylbenzyl)-2',3'-O-isopropylideneinosine | 1217897-05-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 1-benzyl-7-methyl-5'-O-(4-methylbenzyl)-2',3'-O-isopropylideneinosine
• 英文别名: 9-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(4-methylphenyl)methoxymethyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-benzyl-7-methylpurin-9-ium-6-one;iodide
• CAS: 1217897-05-6
• 化学式: C₂₉H₃₃N₄O₅*I
• 分子量: 644.509
• InChiKey: JSGUOCRXMAKNDS-RRMOBMRUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-benzyl-5'-O-(4-methylbenzyl)-2',3'-O-isopropylideneinosine 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-benzyl-7-methyl-5'-O-(4-methylbenzyl)-2',3'-O-isopropylideneinosine
  参考文献：
  名称：

  Intramolecular Cation−π Interactions As the Driving Force To Restrict the Conformation of Certain Nucleosides

  摘要：

  Despite the well-established importance of intermolecular cation-pi interactions in molecular recognition, intramolecular cation-pi interactions have been less studied. Here we describe how the simultaneous presence of an aromatic ring at the 5'-position of an inosine derivative and a positively charged imidazolium ring in the purine base drive the conformation of the nucleoside toward a very major conformer in solution that is stabilized by an intramolecular cation-pi interaction. Therefore, the cation-pi interaction between imidazolium ions and aromatic rings can also be proposed in the design of small molecules where this type of interaction is desirable. The imidazolium ion can be obtained by a simple acidification of the pH of the media. So a simple change in pH can shift the conformational equilibrium from a random to a restricted conformation stabilized by an intramolecular cation-pi interaction. Thus the here described nucleosides can be considered as a new class of pH-dependent conformationally switchable molecules.

  DOI：

  10.1021/jo902677s

文献信息

• Intramolecular Cation−π Interactions As the Driving Force To Restrict the Conformation of Certain Nucleosides
  作者：Elena Casanova、Eva-María Priego、María-Luisa Jimeno、Leire Aguado、Ana Negri、Federico Gago、María-José Camarasa、María-Jesús Pérez-Pérez

  DOI：10.1021/jo902677s

  日期：2010.3.19

  Despite the well-established importance of intermolecular cation-pi interactions in molecular recognition, intramolecular cation-pi interactions have been less studied. Here we describe how the simultaneous presence of an aromatic ring at the 5'-position of an inosine derivative and a positively charged imidazolium ring in the purine base drive the conformation of the nucleoside toward a very major conformer in solution that is stabilized by an intramolecular cation-pi interaction. Therefore, the cation-pi interaction between imidazolium ions and aromatic rings can also be proposed in the design of small molecules where this type of interaction is desirable. The imidazolium ion can be obtained by a simple acidification of the pH of the media. So a simple change in pH can shift the conformational equilibrium from a random to a restricted conformation stabilized by an intramolecular cation-pi interaction. Thus the here described nucleosides can be considered as a new class of pH-dependent conformationally switchable molecules.