5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine

• 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: 5-{3-[4-(triphenylmethyl)phenoxy]prop-1-ynyl}-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-[3-(4-tritylphenoxy)prop-1-ynyl]pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[3-(4-tritylphenoxy)prop-1-ynyl]pyrimidine-2,4-dione
• 化学式: C₃₇H₃₂N₂O₆
• 分子量: 600.671
• InChiKey: WCZKQYDLKVTKPJ-LBFZIJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  碘苷 在 四(三苯基膦)钯 吡啶 、 copper(l) iodide 、 triethylamine trihydrofluoride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 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