5'-deoxypyrazofurin | 143645-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-deoxypyrazofurin
• 英文别名: 5'-Deoxypyrazofurin；3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxamide
• CAS: 143645-19-6
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: ZDFJFGFVFKMTSC-FLLFQEBCSA-N

物化性质

• 沸点：
  506.9±50.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基-5-脱氧-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 palladium on activated charcoal 盐酸 、 对甲苯磺酰叠氮 、 Amberlite IR-120 (H⁺) 、 氨 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 15.0~95.0 ℃ 、413.69 kPa 条件下， 反应 127.5h， 生成 5'-deoxypyrazofurin
  参考文献：
  名称：

  Synthesis and antiviral activity of 5'-deoxypyrazofurin

  摘要：

  In searching for derivatives of pyrazofurin that could display antiviral properties by means that do not require C-5' phosphorylation, 5'-deoxypyrazofurin (3) has been synthesized in six steps from methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(4). Compound 3 was evaluated for antiviral activity against a large number of viruses including herpes-, pox-, myxo-, toga-, arena-, rhabdo-, picorna-, reo-, and retroviruses. Compound 3 proved active against respiratory syncytial virus (in HeLa cells), vaccinia virus (in embryonic skin-muscle fibroblast cells), vesicular stomatitis virus (in HeLa cells), and influenza A virus (in M adin-Darby canine kidney cells) at concentrations (ranging from 4 to 20 mug/mL) that were nontoxic to the confluent host cell cultures.

  DOI：

  10.1021/jm00075a030

文献信息

• Synthesis and antiviral activity of 5'-deoxypyrazofurin
  作者：Xing Chen、Stewart W. Schneller、Satoru Ikeda、Robert Snoeck、Graciela Andrei、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00075a030

  日期：1993.11

  In searching for derivatives of pyrazofurin that could display antiviral properties by means that do not require C-5' phosphorylation, 5'-deoxypyrazofurin (3) has been synthesized in six steps from methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(4). Compound 3 was evaluated for antiviral activity against a large number of viruses including herpes-, pox-, myxo-, toga-, arena-, rhabdo-, picorna-, reo-, and retroviruses. Compound 3 proved active against respiratory syncytial virus (in HeLa cells), vaccinia virus (in embryonic skin-muscle fibroblast cells), vesicular stomatitis virus (in HeLa cells), and influenza A virus (in M adin-Darby canine kidney cells) at concentrations (ranging from 4 to 20 mug/mL) that were nontoxic to the confluent host cell cultures.