N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine | 1311147-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine
• CAS: 1311147-63-3
• 化学式: C₄₄H₄₆N₆O₉
• 分子量: 802.884
• InChiKey: MVQFYKMFKHOYFV-CISTVLBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  185.38
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine 在 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-3'-O-[(2-cyanoethyl)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine
  参考文献：
  名称：

  Nucleobase and Ribose Modifications Control Immunostimulation by a MicroRNA-122-mimetic RNA

  摘要：

  Immune stimulation is a significant hurdle in the development of effective and safe RNA interference therapeutics. Here, we address this problem in the context of a mimic of microRNA-122 by employing novel nucleobase and known 2'-ribose modifications. The nucleobase modifications are analogues of adenosine and guanosine that contain cyclopentyl and propyl minor-groove projections. Via a site-by-site chemical modification analysis, we identify several immunostimulatory 'hot spots' within the miRNA guide strand at which single base modifications significantly reduce immune stimulation. A duplex containing one base modification on each strand proved to be most effective in preventing immune stimulation.

  DOI：

  10.1021/ja202492e
• 作为产物：
  描述：

  2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine
  参考文献：
  名称：

  Nucleobase and Ribose Modifications Control Immunostimulation by a MicroRNA-122-mimetic RNA

  摘要：

  Immune stimulation is a significant hurdle in the development of effective and safe RNA interference therapeutics. Here, we address this problem in the context of a mimic of microRNA-122 by employing novel nucleobase and known 2'-ribose modifications. The nucleobase modifications are analogues of adenosine and guanosine that contain cyclopentyl and propyl minor-groove projections. Via a site-by-site chemical modification analysis, we identify several immunostimulatory 'hot spots' within the miRNA guide strand at which single base modifications significantly reduce immune stimulation. A duplex containing one base modification on each strand proved to be most effective in preventing immune stimulation.

  DOI：

  10.1021/ja202492e