1-[3-O-acetyl-2,5-dideoxy-β-D-glycero-4-eno-4-thiofuranosyl]thymine | 1017605-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[3-O-acetyl-2,5-dideoxy-β-D-glycero-4-eno-4-thiofuranosyl]thymine
• 英文别名: [(3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-methylidenethiolan-3-yl] acetate
• CAS: 1017605-13-8
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: BGWRKGNETZTOJA-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-O-acetyl-2,5-dideoxy-β-D-glycero-4-eno-4-thiofuranosyl]thymine 在 氨 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 4′-Substituted 4′-Thiothymidines: A New Entry Based on Nucleophilic Substitution of the 4′-Acetoxy Group

  摘要：

  Diacetoxylation of 1-(2,5-dideoxy-beta-L-glycero-pent-4-eno-4-thiofuranosyl)thymine (13) with Pb(OAc)(4) allowed introduction of an acetoxy leaving group to the 4 '-position. Nucleophilic substitution of the resulting 4 '-acetoxy derivative (14) with silicon reagents enabled us to prepare the 4 '-phenylthio (17a), 4 '-azido (18a), 4 '-methoxy (20a), and 4 '-allyl (21a) analogues of 4 '-thiothymidine. 4 '-Cyano (25a) and 4 '-ethynyl (31) nucleosides were also synthesized from 3 ',5 '-bis-O-TBDMS derivative (24). Among novel 4 '-substituted 4 '-thiothymidines, the 4 '-azido (33), 4 '-cyano (36), and 4 '-ethynyl (37) derivatives were found to show potent inhibitory activity against HIV-1 and HIV-2. It is noteworthy that 36 and 37 were also inhibitory against replication of HIV variant resistant to 3TC (HIV-1(M184V)), being as potent as against HIV-1(IIIB).

  DOI：

  10.1021/jm070824s
• 作为产物：
  描述：

  1-[2-deoxy-3,5-di-O-acetyl-4-thio-β-D-ribofuranosyl]thymine 在 敌草腈 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以3.29 g的产率得到1-[3-O-acetyl-2,5-dideoxy-β-D-glycero-4-eno-4-thiofuranosyl]thymine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 4′-Substituted 4′-Thiothymidines: A New Entry Based on Nucleophilic Substitution of the 4′-Acetoxy Group

  摘要：

  Diacetoxylation of 1-(2,5-dideoxy-beta-L-glycero-pent-4-eno-4-thiofuranosyl)thymine (13) with Pb(OAc)(4) allowed introduction of an acetoxy leaving group to the 4 '-position. Nucleophilic substitution of the resulting 4 '-acetoxy derivative (14) with silicon reagents enabled us to prepare the 4 '-phenylthio (17a), 4 '-azido (18a), 4 '-methoxy (20a), and 4 '-allyl (21a) analogues of 4 '-thiothymidine. 4 '-Cyano (25a) and 4 '-ethynyl (31) nucleosides were also synthesized from 3 ',5 '-bis-O-TBDMS derivative (24). Among novel 4 '-substituted 4 '-thiothymidines, the 4 '-azido (33), 4 '-cyano (36), and 4 '-ethynyl (37) derivatives were found to show potent inhibitory activity against HIV-1 and HIV-2. It is noteworthy that 36 and 37 were also inhibitory against replication of HIV variant resistant to 3TC (HIV-1(M184V)), being as potent as against HIV-1(IIIB).

  DOI：

  10.1021/jm070824s