3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methyl-4-O-(4-nitrophenyl)uridine | 402518-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methyl-4-O-(4-nitrophenyl)uridine
• CAS: 402518-16-5
• 化学式: C₂₈H₄₃N₃O₈Si₂
• 分子量: 605.836
• InChiKey: ZBXPAOSBUVIDLS-CYUUXAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  124.18
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methyl-4-O-(4-nitrophenyl)uridine 在 四丁基氟化铵 、 四甲基胍 、 2-硝基苯甲醛肟 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 2'-deoxy-2'-C-β-methyluridine
  参考文献：
  名称：

  Influence of conformationally restricted pyrimidines on the activity of 10–23 DNAzymes

  摘要：

  The catalytic core of a 10-23 DNAzyme was modified introducing conformationally restricted nucleosides such as (2'R)-, (2'S)-2'-deoxy-2'-C-methyluridine, (2'R)-, (2'S)-2'-deoxy-2'-C-methylcytidine, 2,2'-anhydrouridine and LNA-C, in one, two or three positions. Catalytic activities under pseudo first order conditions were compared at different Mg2+ concentrations using a short RNA substrate. At low Mg2+ concentrations, triple modified DNAzymes with similar kinetic performance to that displayed by the non-modified control were identified. In the search for a partial explanation of the obtained results, in silico studies were carried out in order to explore the conformational behavior of 2'-deoxy-2'-C-methyl-pyrimidines in the context of a loop structure, suggesting that at least partial flexibility is needed for the maintenance of activity. Finally, the modified 2'-C-methyl DNAzyme activity was tested assessing the inhibition of Stat3 expression and the decrease in cell proliferation using the human breast cancer cell line T47D. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.047
• 作为产物：
  描述：

  1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 在 氢气 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methyl-4-O-(4-nitrophenyl)uridine
  参考文献：
  名称：

  Influence of conformationally restricted pyrimidines on the activity of 10–23 DNAzymes

  摘要：

  The catalytic core of a 10-23 DNAzyme was modified introducing conformationally restricted nucleosides such as (2'R)-, (2'S)-2'-deoxy-2'-C-methyluridine, (2'R)-, (2'S)-2'-deoxy-2'-C-methylcytidine, 2,2'-anhydrouridine and LNA-C, in one, two or three positions. Catalytic activities under pseudo first order conditions were compared at different Mg2+ concentrations using a short RNA substrate. At low Mg2+ concentrations, triple modified DNAzymes with similar kinetic performance to that displayed by the non-modified control were identified. In the search for a partial explanation of the obtained results, in silico studies were carried out in order to explore the conformational behavior of 2'-deoxy-2'-C-methyl-pyrimidines in the context of a loop structure, suggesting that at least partial flexibility is needed for the maintenance of activity. Finally, the modified 2'-C-methyl DNAzyme activity was tested assessing the inhibition of Stat3 expression and the decrease in cell proliferation using the human breast cancer cell line T47D. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.047