5'-<(tert-butyldiphenyl)silyl>-N⁴-succinyl-2',3'-dideoxycytidine | 170164-16-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-<(tert-butyldiphenyl)silyl>-N⁴-succinyl-2',3'-dideoxycytidine
• CAS: 170164-16-6
• 化学式: C₂₉H₃₅N₃O₆Si
• 分子量: 549.699
• InChiKey: YRFITJIWODZSNX-HFZDXXHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119.75
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5'-<(tert-butyldiphenyl)silyl>-N⁴-succinyl-2',3'-dideoxycytidine 、 H-Trp-Val-Sta-NH-CH(Ph)-CH2-Ph 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以16%的产率得到5'-<(tert-butyldiphenyl)silyl>-N⁴-(1,4-dioxobutyl-Trp-Val-Sta-CH(Ph)-CH2Ph)-2',3'-dideoxycytidine
  参考文献：
  名称：

  Peptide-Nucleoside Conjugates: Synthesis and Anti-HIV Activities

  摘要：

  New peptide-nucleosides which consist of an anti-RT nucleoside and anti-protease peptide moieties, were designed in order to investigate their anti-HIV-1 properties. The synthesis of these new analogues was achieved using BOP coupling reagent which avoided the protection and deprotection steps of the 5'-OH group of the nucleoside part. These new compounds tested on MT(4) infected cells show no increase in anti-HIV activities compared to that of the component pieces. Interestingly we found that the 5'-(tert-butyldiphenyl)silyl analogues show anti-HIV activities equivalent to that of the 5'-free OH corresponding compounds. This result suggests a possible interaction of these compounds at a non-substrate binding site of the reverse transcriptase.

  DOI：

  10.1080/15257779508010699
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5'-<(tert-butyldiphenyl)silyl>-N⁴-succinyl-2',3'-dideoxycytidine
  参考文献：
  名称：

  Peptide-Nucleoside Conjugates: Synthesis and Anti-HIV Activities

  摘要：

  New peptide-nucleosides which consist of an anti-RT nucleoside and anti-protease peptide moieties, were designed in order to investigate their anti-HIV-1 properties. The synthesis of these new analogues was achieved using BOP coupling reagent which avoided the protection and deprotection steps of the 5'-OH group of the nucleoside part. These new compounds tested on MT(4) infected cells show no increase in anti-HIV activities compared to that of the component pieces. Interestingly we found that the 5'-(tert-butyldiphenyl)silyl analogues show anti-HIV activities equivalent to that of the 5'-free OH corresponding compounds. This result suggests a possible interaction of these compounds at a non-substrate binding site of the reverse transcriptase.

  DOI：

  10.1080/15257779508010699