3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine | 877643-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine
• CAS: 877643-02-2
• 化学式: C₄₉H₅₈N₂O₇Si₂
• 分子量: 843.18
• InChiKey: YZLDJMUIUWVETD-VURFOUDESA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.59
• 重原子数：
  60.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  101.01
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine 在 triethylamine trihydrofluoride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以77%的产率得到5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine
  参考文献：
  名称：

  5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: evaluation of structure–anti-HSV-1 activity relationship

  摘要：

  Four 5-alkynyl-2-deoxyuridines containing different bulky substituents and flexible linkers between the triple bond and the aromatic residue have been prepared and tested against HSV-1 in Vero cells. Two nucleosides containing carbonyl groups, 5-(4-benzoylphenoxypropyn-1-yl)-2'-deoxyutidine (19a) and 5-(estron-3-yloxypropyn-1-yl)-2'-deoxyuridine (19c), showed low cytotoxicity and moderate antiviral activity. The flexible linker appears not to be favorable for antiviral properties of 5-alkynyl-2'deoxyuridines: 5-[(perylen-3-yl)methoxypropyn-1-yl]-2'-deoxyuridine (19d) showed considerable cytotoxicity and no antiviral activity in contrast to the active and nontoxic 5-(perylen-3-ylethynyl)-2'-deoxyuridine (9), a nucleoside with a rigid triple-bond-connection of the aromatic system to the nucleobase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.057
• 作为产物：
  描述：

  三苯甲基苯酚 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 64.0h， 生成 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine
  参考文献：
  名称：

  5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: evaluation of structure–anti-HSV-1 activity relationship

  摘要：

  Four 5-alkynyl-2-deoxyuridines containing different bulky substituents and flexible linkers between the triple bond and the aromatic residue have been prepared and tested against HSV-1 in Vero cells. Two nucleosides containing carbonyl groups, 5-(4-benzoylphenoxypropyn-1-yl)-2'-deoxyutidine (19a) and 5-(estron-3-yloxypropyn-1-yl)-2'-deoxyuridine (19c), showed low cytotoxicity and moderate antiviral activity. The flexible linker appears not to be favorable for antiviral properties of 5-alkynyl-2'deoxyuridines: 5-[(perylen-3-yl)methoxypropyn-1-yl]-2'-deoxyuridine (19d) showed considerable cytotoxicity and no antiviral activity in contrast to the active and nontoxic 5-(perylen-3-ylethynyl)-2'-deoxyuridine (9), a nucleoside with a rigid triple-bond-connection of the aromatic system to the nucleobase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.057