(+/-)-5-benzyl-5-ethyl-4-(4'-methoxybenzyloxy)-5H-1,2-oxathiole-2,2-dioxide | 1127304-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-5-benzyl-5-ethyl-4-(4'-methoxybenzyloxy)-5H-1,2-oxathiole-2,2-dioxide
• 英文别名: 5-Benzyl-5-ethyl-4-[(4-methoxyphenyl)methoxy]oxathiole 2,2-dioxide
• CAS: 1127304-94-2
• 化学式: C₂₀H₂₂O₅S
• 分子量: 374.458
• InChiKey: VEAXFFYRZVYQGC-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C(Solvent: Water; Ethanol)
• 沸点：
  556.5±50.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-5-benzyl-5-ethyl-4-oxo-1,2-oxathiolane-2,2-dioxide 、 4-甲氧基溴苄 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以40%的产率得到(+/-)-5-benzyl-5-ethyl-4-(4'-methoxybenzyloxy)-5H-1,2-oxathiole-2,2-dioxide
  参考文献：
  名称：

  4-Benzyloxy-γ-Sultone Derivatives: Discovery of a Novel Family of Non-Nucleoside Inhibitors of Human Cytomegalovirus and Varicella Zoster Virus

  摘要：

  We report the synthesis and antiviral activity of a new family of non-nucleoside antivirals, derived from the 4-keto-1,2-oxathiole-2,2-dioxide (beta-keto-gamma-sultone) heterocyclic system. Several 4- and 5-substituted-5H-1,2-oxathiole-2,2-dioxide derivatives were found to have a selective inhibitory activity against human cytomegalovirus (HCMV) and varicella zoster virus (VZV) replication in vitro, being inactive against a variety of other DNA and RNA viruses. A structure-activity relationship (SAR) study showed that the presence of a benzyl at the 5 position and a benzyloxy substituent at the 4 position are a prerequisite for anti-HCMV and VZV activity. The novel compounds do not show cross-resistance against a wide variety of mutant drug-resistant HCMV strains, pointing to a novel mechanism of antiviral action.

  DOI：

  10.1021/jm8014662

文献信息

• 4-Benzyloxy-γ-Sultone Derivatives: Discovery of a Novel Family of Non-Nucleoside Inhibitors of Human Cytomegalovirus and Varicella Zoster Virus
  作者：Sonia De Castro、Carlos García-Aparicio、Graciela Andrei、Robert Snoeck、Jan Balzarini、María-José Camarasa、Sonsoles Velázquez

  DOI：10.1021/jm8014662

  日期：2009.3.26

  We report the synthesis and antiviral activity of a new family of non-nucleoside antivirals, derived from the 4-keto-1,2-oxathiole-2,2-dioxide (beta-keto-gamma-sultone) heterocyclic system. Several 4- and 5-substituted-5H-1,2-oxathiole-2,2-dioxide derivatives were found to have a selective inhibitory activity against human cytomegalovirus (HCMV) and varicella zoster virus (VZV) replication in vitro, being inactive against a variety of other DNA and RNA viruses. A structure-activity relationship (SAR) study showed that the presence of a benzyl at the 5 position and a benzyloxy substituent at the 4 position are a prerequisite for anti-HCMV and VZV activity. The novel compounds do not show cross-resistance against a wide variety of mutant drug-resistant HCMV strains, pointing to a novel mechanism of antiviral action.