(+/-)-1,2,3,4-tetrahydronaphthalene-2-spiro-5'-(4'-benzyloxy-5'H-1',2'-oxathiole-2',2'-dioxide) | 1127304-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-1,2,3,4-tetrahydronaphthalene-2-spiro-5'-(4'-benzyloxy-5'H-1',2'-oxathiole-2',2'-dioxide)
• 英文别名: 4-Benzyloxyspiro[oxathiole-5,2'-tetralin] 2,2-dioxide；4'-phenylmethoxyspiro[2,4-dihydro-1H-naphthalene-3,5'-oxathiole] 2',2'-dioxide
• CAS: 1127304-61-3
• 化学式: C₁₉H₁₈O₄S
• 分子量: 342.416
• InChiKey: QRRSGSDFJJCJRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-1,2,3,4-tetrahydronaphthalene-2-spiro-5'-(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44%的产率得到(+/-)-1,2,3,4-tetrahydronaphthalene-2-spiro-5'-(4'-benzyloxy-5'H-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.