(+/-)-5-benzyl-5-isopropyl-4-oxo-1,2-oxathiolane-2,2-dioxide | 1127304-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: (+/-)-5-benzyl-5-isopropyl-4-oxo-1,2-oxathiolane-2,2-dioxide
• 英文别名: 5-Benzyl-2,2-dioxo-5-propan-2-yloxathiolan-4-one
• CAS: 1127304-42-0
• 化学式: C₁₃H₁₆O₄S
• 分子量: 268.334
• InChiKey: OCLHQFVGPDRELL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-5-benzyl-5-isopropyl-4-oxo-1,2-oxathiolane-2,2-dioxide 、 溴甲苯 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以63%的产率得到(+/-)-5-benzyl-4-benzyloxy-5-isopropyl-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
• 作为产物：
  描述：

  (+/-)-4-amino-5-benzyl-5-isopropyl-5H-1,2-oxathiole-2,2-dioxide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以81%的产率得到(+/-)-5-benzyl-5-isopropyl-4-oxo-1,2-oxathiolane-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