1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-6-(phenylselenenyl)uracil | 136631-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-6-(phenylselenenyl)uracil
• 英文别名: 1-[2-[tert-butyl(dimethyl)silyl]oxyethoxymethyl]-6-phenylselanylpyrimidine-2,4-dione
• CAS: 136631-96-4
• 化学式: C₁₉H₂₈N₂O₄SeSi
• 分子量: 455.488
• InChiKey: XWVZXHSNGPPPQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-6-(phenylselenenyl)uracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以86%的产率得到1-<(2-hydroxyethoxy)methyl>-6-(phenylselenenyl)uracil
  参考文献：
  名称：

  Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes

  摘要：

  Several 6-phenylselenenyl-substituted acyclouridine derivatives were prepared for evaluation as antiviral agents. Lithiation of the tert-butyldimethylsilyl-protected acyclonucleosides 4a-f with lithium diisopropylamide at -78-degrees-C, followed by reaction with diphenyl diselenide as an electrophile, and subsequent removal of the protecting group with tetra n-butylammonium fluoride gave 1-[(2-hydroxyethoxy)methyl]-6-(phenylselenenyl)uracils 6a-f in 50-70% overall yield. The potency and spectrum of activity of compounds 6a-f against HIV-1 in vitro was similar to HEPT (1), a related 6-phenylthio acyclonucleoside. However, whereas HEPT inhibited HIV-1 reverse transcriptase, the selenium-containing derivatives were ineffective, suggesting a different mechanism of action. Of significance was the finding that the 6-phenylselenenyl acyclonucleosides inhibited also HIV-2 in primary human lymphocytes.

  DOI：

  10.1021/jm00115a022
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-6-(phenylselenenyl)uracil
  参考文献：
  名称：

  Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes

  摘要：

  Several 6-phenylselenenyl-substituted acyclouridine derivatives were prepared for evaluation as antiviral agents. Lithiation of the tert-butyldimethylsilyl-protected acyclonucleosides 4a-f with lithium diisopropylamide at -78-degrees-C, followed by reaction with diphenyl diselenide as an electrophile, and subsequent removal of the protecting group with tetra n-butylammonium fluoride gave 1-[(2-hydroxyethoxy)methyl]-6-(phenylselenenyl)uracils 6a-f in 50-70% overall yield. The potency and spectrum of activity of compounds 6a-f against HIV-1 in vitro was similar to HEPT (1), a related 6-phenylthio acyclonucleoside. However, whereas HEPT inhibited HIV-1 reverse transcriptase, the selenium-containing derivatives were ineffective, suggesting a different mechanism of action. Of significance was the finding that the 6-phenylselenenyl acyclonucleosides inhibited also HIV-2 in primary human lymphocytes.

  DOI：

  10.1021/jm00115a022