2-(methanesulfonyloxy)-4-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-2-butyronitrile | 1056299-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-(methanesulfonyloxy)-4-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-2-butyronitrile
• CAS: 1056299-21-8
• 化学式: C₁₈H₃₉NO₅SSi₂
• 分子量: 437.748
• InChiKey: YRBQNSIGNQLNDP-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  2-(methanesulfonyloxy)-4-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-2-butyronitrile 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以75%的产率得到4-amino-5-(tert-butyldimethylsilyloxyeth-2-yl)-5-(tert-butyldimethylsilyloxymethyl)-5H-1,2-oxathiole-2,2-dioxide
  参考文献：
  名称：

  4′′-Benzoylureido-TSAO Derivatives as Potent and Selective Non-Nucleoside HCMV Inhibitors. Structure−Activity Relationship and Mechanism of Antiviral Action

  摘要：

  Analogues of the 4"-benzoyl-ureido-TSAO derivative (1) modified at different positions have been prepared and evaluated against wild-type strains of HCMV and murine cytomegalovirus (MCMV) in cell culture. In addition, the activity of the most active derivatives against several drug-resistant HCMV mutants has been determined. A stringent structure-antiviral activity relationship was observed for the 4"-benzoylureido-TSAO derivatives for which the concomitant presence of a highly lipophilic substituent at both 2'- and 5'-positions was required to fully preserve the antihuman cytomegalovirus efficacy. Time-of-addition studies and HCMV immediately early and early gene expression studies revealed a target at the time of viral DNA synthesis, although direct inhibition of HCMV-encoded DNA polymerase could not be observed in cell-free assays. Lack of cross-resistance against a broad variety of mutant HCMV strains points to an antiviral target that is different from those drugs that are currently approved for clinical use.

  DOI：

  10.1021/jm800050t
• 作为产物：
  描述：

  、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以298 mg的产率得到2-(methanesulfonyloxy)-4-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-2-butyronitrile
  参考文献：
  名称：

  4′′-Benzoylureido-TSAO Derivatives as Potent and Selective Non-Nucleoside HCMV Inhibitors. Structure−Activity Relationship and Mechanism of Antiviral Action

  摘要：

  Analogues of the 4"-benzoyl-ureido-TSAO derivative (1) modified at different positions have been prepared and evaluated against wild-type strains of HCMV and murine cytomegalovirus (MCMV) in cell culture. In addition, the activity of the most active derivatives against several drug-resistant HCMV mutants has been determined. A stringent structure-antiviral activity relationship was observed for the 4"-benzoylureido-TSAO derivatives for which the concomitant presence of a highly lipophilic substituent at both 2'- and 5'-positions was required to fully preserve the antihuman cytomegalovirus efficacy. Time-of-addition studies and HCMV immediately early and early gene expression studies revealed a target at the time of viral DNA synthesis, although direct inhibition of HCMV-encoded DNA polymerase could not be observed in cell-free assays. Lack of cross-resistance against a broad variety of mutant HCMV strains points to an antiviral target that is different from those drugs that are currently approved for clinical use.

  DOI：

  10.1021/jm800050t