4-N-(8-aminoquinolin-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-(8-aminoquinolin-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine
• 英文别名: 4-[(8-aminoquinolin-2-yl)methylamino]-1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]pyrimidin-2-one
• 化学式: C₃₁H₄₉N₅O₄Si₂
• 分子量: 611.932
• InChiKey: RSZYWPHZWJRLDE-ZWEKWIFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-nitroquinoline-2-carbonitrile 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、379.21 kPa 条件下， 反应 21.5h， 生成 4-N-(8-aminoquinolin-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine
  参考文献：
  名称：

  Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites

  摘要：

  A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via H-1 NMR complexation studies in 5% DMSO-d(6)-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure -function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.

  DOI：

  10.1021/jo0501689

文献信息

• Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites
  作者：Jordan R. Quinn、Steven C. Zimmerman

  DOI：10.1021/jo0501689

  日期：2005.9.1

  A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via H-1 NMR complexation studies in 5% DMSO-d(6)-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure -function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.