3,4-di-O-acetyl-2-thio-1-O,2-S-(1,2,3,6-tetrahydro-2,6-dioxo-4,5-pyrimidinediyl)-β-L-rhamnopyranose

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,4-di-O-acetyl-2-thio-1-O,2-S-(1,2,3,6-tetrahydro-2,6-dioxo-4,5-pyrimidinediyl)-β-L-rhamnopyranose
• 英文别名: 3,4-Di-O-acetyl-2-thio-1-O-2,S-(1,2,3,6-tetrahydro-2,6-dioxo-4,5-pyrimidinediyl)-beta-L-rhamnopyranose；[(1R,10R,11R,12S,13S)-11-acetyloxy-13-methyl-5,7-dioxo-2,14-dioxa-9-thia-4,6-diazatricyclo[8.4.0.03,8]tetradec-3(8)-en-12-yl] acetate
• 化学式: C₁₄H₁₆N₂O₈S
• 分子量: 372.356
• InChiKey: CHQDYFFRBKOLPX-HTRIKHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 、 N,2-bis(thiophthalimido)barbituric acid 在 2,6-二甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以35%的产率得到3,4-di-O-acetyl-2-thio-1-O,2-S-(1,2,3,6-tetrahydro-2,6-dioxo-4,5-pyrimidinediyl)-β-L-rhamnopyranose
  参考文献：
  名称：

  The Synthesis and Biological Evaluation of Novel Bridging Nucleoside Analogues

  摘要：

  Novel bridging nucleoside analogues were prepared by cycloaddition reactions between pyranose glycals and barbiturate-derived, reactive thionoimides in modest yields. In all of the reactions conducted, the major cycloadducts obtained were the bottom faced adducts resulting from endo addition to the glycal. The adducts were stable to a variety of acidic reaction conditions and several of the compounds showed moderate activities against HIV-1 in primary human lymphocytes. One compound displayed anti-herpes simplex virus type-1 activity in Vero cells. Cytotoxicity measurements were also obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00278-4

文献信息

• The Synthesis and Biological Evaluation of Novel Bridging Nucleoside Analogues
  作者：Cecilia H. Marzabadi、Richard W. Franck、Raymond F. Schinazi

  DOI：10.1016/s0968-0896(01)00278-4

  日期：2002.2

  Novel bridging nucleoside analogues were prepared by cycloaddition reactions between pyranose glycals and barbiturate-derived, reactive thionoimides in modest yields. In all of the reactions conducted, the major cycloadducts obtained were the bottom faced adducts resulting from endo addition to the glycal. The adducts were stable to a variety of acidic reaction conditions and several of the compounds showed moderate activities against HIV-1 in primary human lymphocytes. One compound displayed anti-herpes simplex virus type-1 activity in Vero cells. Cytotoxicity measurements were also obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.