3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanyl)-ribavirin | 140891-04-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanyl)-ribavirin
• 英文别名: 1-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1H-1,2,4-triazole-3-carboxamide；1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-1,2,4-triazole-3-carboxamide
• CAS: 140891-04-9
• 化学式: C₂₀H₃₈N₄O₆Si₂
• 分子量: 486.716
• InChiKey: OKQKCDKZHGYWSE-WOCWXWTJSA-N

物化性质

• 熔点：
  40-41 °C
• 沸点：
  546.6±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanyl)-ribavirin 、 硫代氯甲酸苯酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  In Search of New Inhibitors of HIV-1 Replication: Synthesis and Study of 1-(2′-Deoxy-β-D-Ribofuranosyl)-1,2,4-Triazole-3-Carboxamide as a Selective Viral Mutagenic Agent

  摘要：

  With the emergence of HIV strains resistant or cross-resistant to nearly all antiretroviral regimen, novel therapy approaches have to be considered. As a part of our current work on viral mutagenic compounds, we prepared 1-(2' -deoxy-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (2' -deoxy-ribavirin) and its 5' -triphosphate derivative. The nucleoside mutagenic activity was evaluated on HIV-1 NL4-3 in CEMx174 cell culture. After 2.5 months, no reduction on HIV-1 viability was observed. On the other hand, in vitro experiments with purified HIV-1 RT demonstrated that the triphosphate analog can be incorporated opposite to several natural nucleosides.

  DOI：

  10.1080/15257770701490902
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 利巴韦林 在 吡啶 作用下， 反应 23.5h， 以91%的产率得到3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanyl)-ribavirin
  参考文献：
  名称：

  Oligomer conjugates of heteropentacyclic nucleosides

  摘要：

  本发明提供了通过共价连接水溶性寡聚体化学修饰的小分子药物。

  公开号：

  US09149538B2

文献信息

• In Search of New Inhibitors of HIV-1 Replication: Synthesis and Study of 1-(2′-Deoxy-β-D-Ribofuranosyl)-1,2,4-Triazole-3-Carboxamide as a Selective Viral Mutagenic Agent
  作者：V. Vivet-Boudou、J.-C. Paillart、A. Burger、R. Marquet

  DOI：10.1080/15257770701490902

  日期：2007.11.26

  With the emergence of HIV strains resistant or cross-resistant to nearly all antiretroviral regimen, novel therapy approaches have to be considered. As a part of our current work on viral mutagenic compounds, we prepared 1-(2' -deoxy-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (2' -deoxy-ribavirin) and its 5' -triphosphate derivative. The nucleoside mutagenic activity was evaluated on HIV-1 NL4-3 in CEMx174 cell culture. After 2.5 months, no reduction on HIV-1 viability was observed. On the other hand, in vitro experiments with purified HIV-1 RT demonstrated that the triphosphate analog can be incorporated opposite to several natural nucleosides.
• Oligomer conjugates of heteropentacyclic nucleosides
  申请人：NEKTAR THERAPEUTICS

  公开号：US09149538B2

  公开（公告）日：2015-10-06

  The invention provides small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer.

  本发明提供了通过共价连接水溶性寡聚体化学修饰的小分子药物。