methyl 5-deoxy-5-(6-propyluracil-2-yl)thio-β-D-ribofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-5-(6-propyluracil-2-yl)thio-β-D-ribofuranoside
• 英文别名: 2-[[(2S,3S,4R,5R)-3,4-dihydroxy-5-methoxyoxolan-2-yl]methylsulfanyl]-4-propyl-1H-pyrimidin-6-one
• 化学式: C₁₃H₂₀N₂O₅S
• 分子量: 316.378
• InChiKey: DQDHDGRXDDNFNO-HJQYOEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙硫氧嘧啶 在 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 methyl 5-deoxy-5-(6-propyluracil-2-yl)thio-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Anti-HBV Activity of Thiouracils Linked via S and N-1 to the 5-Position of Methyl β-D-Ribofuranoside

  摘要：

  Reverse nucleoside derivatives of 2-(methylsulfanyl)uracils 6a-d were prepared by treating of the sodium salt of 2-(methylsulfanyl)uracils (5a-d) with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-beta-D-ribofuranoside (2). The alkylation of 2-thiouracils 4a-d with methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribofuranoside (3) afforded the corresponding S-ribofuranoside derivatives 8a-d. Deisopropylidenation of 6a-d and 8a-d afforded the corresponding deprotected derivatives 7a-d and 9a-d, respectively. The Anti-HBV activity of selected compounds was studied.

  DOI：

  10.1081/ncn-120026404

文献信息

• Synthesis and Anti-HBV Activity of Thiouracils Linked via S and N-1 to the 5-Position of Methyl β-D-Ribofuranoside
  作者：Adel A.-H. Abdel-Rahman、Ahmed E.-S. Abdel-Megied、Adel E.-S. Goda、Ibrahim F. Zeid、El Sayed H. El Ashry

  DOI：10.1081/ncn-120026404

  日期：2003.11

  Reverse nucleoside derivatives of 2-(methylsulfanyl)uracils 6a-d were prepared by treating of the sodium salt of 2-(methylsulfanyl)uracils (5a-d) with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-beta-D-ribofuranoside (2). The alkylation of 2-thiouracils 4a-d with methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribofuranoside (3) afforded the corresponding S-ribofuranoside derivatives 8a-d. Deisopropylidenation of 6a-d and 8a-d afforded the corresponding deprotected derivatives 7a-d and 9a-d, respectively. The Anti-HBV activity of selected compounds was studied.