2',3',5'-tri-O-acetyl-5-methyl-3-(β-D-ribofuranosyl)-1,2,4-triazolo<2,3-a>purine-9-thione | 219637-58-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3',5'-tri-O-acetyl-5-methyl-3-(β-D-ribofuranosyl)-1,2,4-triazolo<2,3-a>purine-9-thione
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-methyl-9-sulfanylidene-[1,2,4]triazolo[1,5-a]purin-3-yl)oxolan-2-yl]methyl acetate
• CAS: 219637-58-8
• 化学式: C₁₈H₂₀N₆O₇S
• 分子量: 464.459
• InChiKey: VYOTXKXHSPJNRQ-XKVFNRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-5-methyl-3-(β-D-ribofuranosyl)-1,2,4-triazolo<2,3-a>purine-9-thione 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以70%的产率得到5-methyl-3-(β-D-ribofuranosyl)-1,2,4-triazolo<2,3-a>purine-9-thione
  参考文献：
  名称：

  Antiviral Oligo- and Polyribonucleotides Containing Selected Triazolo[2,3-a]purines

  摘要：

  Several amphipathic (hydrophobic base, hydrophilic backbone) polyribonucleotides have recently been shown to have potent antiviral activity against HIV and human cytomegalovirus (HCMV). The working hypothesis developed during these studies was that the ability to form an ordered, non-hydrogen-bonded array in solution was an important criterion for activity. To explore further the role of structure and molecular size on the inhibition of virus replication, one new polynucleotide and two 32-mer oligonucleotides based on the triazolo[2,3-a]purine ring system have now been prepared. High-molecular-weight polynucleotide 4a (PTPR) and sulfur-containing 32-mer 5b (TTPR) were moderately active against HIV but showed greater potency against HDMV than ganciclovir. Both 4a and 5b gave clear evidence of cooperative melting behavior, whereas inactive 32-mer 5a showed no such behavior.

  DOI：

  10.1021/jm9802057
• 作为产物：
  描述：

  2',3',5'-tri-O-acetyl-5H-9-oxo-3-(β-D-ribofuranosyl)-1,2,4-triazolo<2,3-a>purine 在 劳森试剂 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 2',3',5'-tri-O-acetyl-5-methyl-3-(β-D-ribofuranosyl)-1,2,4-triazolo<2,3-a>purine-9-thione
  参考文献：
  名称：

  Antiviral Oligo- and Polyribonucleotides Containing Selected Triazolo[2,3-a]purines

  摘要：

  Several amphipathic (hydrophobic base, hydrophilic backbone) polyribonucleotides have recently been shown to have potent antiviral activity against HIV and human cytomegalovirus (HCMV). The working hypothesis developed during these studies was that the ability to form an ordered, non-hydrogen-bonded array in solution was an important criterion for activity. To explore further the role of structure and molecular size on the inhibition of virus replication, one new polynucleotide and two 32-mer oligonucleotides based on the triazolo[2,3-a]purine ring system have now been prepared. High-molecular-weight polynucleotide 4a (PTPR) and sulfur-containing 32-mer 5b (TTPR) were moderately active against HIV but showed greater potency against HDMV than ganciclovir. Both 4a and 5b gave clear evidence of cooperative melting behavior, whereas inactive 32-mer 5a showed no such behavior.

  DOI：

  10.1021/jm9802057