9-(2',3'-O-isopropylidene-β-D-ribofuranos-1'-yl)purine-8-thione | 1274898-74-6

• 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: 9-(2',3'-O-isopropylidene-β-D-ribofuranos-1'-yl)purine-8-thione
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-7H-purine-8-thione
• CAS: 1274898-74-6
• 化学式: C₁₃H₁₆N₄O₄S
• 分子量: 324.36
• InChiKey: IXLUOUAPTBQPCP-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(2',3'-O-isopropylidene-β-D-ribofuranos-1'-yl)purine-8-thione 、 3-(chloromethyl)-6-bromocoumarin 在 氨 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 以62%的产率得到8-(6'-bromocoumarin-3'-yl)methylthio-9-(2'',3''-O-isopropylidene-β-D-ribofuranos-1''-yl)purine
  参考文献：
  名称：

  Coumarin−Purine Ribofuranoside Conjugates as New Agents against Hepatitis C Virus

  摘要：

  About 3% of world's population is infected by the hepatitis C virus (HCV), for which prophylactic vaccine is not available yet. Nowadays, pegylated interferon-a and ribavirin are commonly used to treat HCV; unfortunately these drugs often produce significant side effects. Upon the desperate need of anti-HCV drugs, a plan to establish a new compound library was set that included leads with high antiviral activity, good hydrophilicity, yet low toxicity. Accordingly, 26 new conjugated compounds were synthesized through the chemical coupling of various 9-(beta-D-ribofuranosyl)purine-8-thiones with 3-(chloromethyl)coumarins bearing various substitucnts. A -SCH2- unit was used to link the coumarin and the purine moieties. The three hydroxyl groups at the 2'-, 3'-, and 5'-positions were selectively protected with an acyl or acetal group in these coumarin-purine ribofuranosides. Their anti-HCV and cytostatic determination assays were performed, and the structure activity relationship was established. Three conjugates in the family of 8-(coumarin-3'-yl)methylthio-9-(beta-D-ribofuranos-1 ''-yl)purine possessed an appealing ability to inhibit HCV replication with EC50 between 5.5 and 6.6 mu M and EC90 of similar to 20 mu M. These data in the new compound library provide clues for the future in the development of anti-HCV leads for viral eradication.

  DOI：

  10.1021/jm101337v
• 作为产物：
  描述：

  四乙酰核糖 在 N,O-双三甲硅基乙酰胺 、 氨 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 78.5h， 生成 9-(2',3'-O-isopropylidene-β-D-ribofuranos-1'-yl)purine-8-thione
  参考文献：
  名称：

  Coumarin−Purine Ribofuranoside Conjugates as New Agents against Hepatitis C Virus

  摘要：

  About 3% of world's population is infected by the hepatitis C virus (HCV), for which prophylactic vaccine is not available yet. Nowadays, pegylated interferon-a and ribavirin are commonly used to treat HCV; unfortunately these drugs often produce significant side effects. Upon the desperate need of anti-HCV drugs, a plan to establish a new compound library was set that included leads with high antiviral activity, good hydrophilicity, yet low toxicity. Accordingly, 26 new conjugated compounds were synthesized through the chemical coupling of various 9-(beta-D-ribofuranosyl)purine-8-thiones with 3-(chloromethyl)coumarins bearing various substitucnts. A -SCH2- unit was used to link the coumarin and the purine moieties. The three hydroxyl groups at the 2'-, 3'-, and 5'-positions were selectively protected with an acyl or acetal group in these coumarin-purine ribofuranosides. Their anti-HCV and cytostatic determination assays were performed, and the structure activity relationship was established. Three conjugates in the family of 8-(coumarin-3'-yl)methylthio-9-(beta-D-ribofuranos-1 ''-yl)purine possessed an appealing ability to inhibit HCV replication with EC50 between 5.5 and 6.6 mu M and EC90 of similar to 20 mu M. These data in the new compound library provide clues for the future in the development of anti-HCV leads for viral eradication.

  DOI：

  10.1021/jm101337v