1-(2-deoxy-α-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone | 75670-15-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2-deoxy-α-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone
• 英文别名: 1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylsulfanylpyrimidin-2-one
• CAS: 75670-15-4
• 化学式: C₁₀H₁₄N₂O₄S
• 分子量: 258.298
• InChiKey: KEIQSLRUOBLVRD-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl>-5-(methylmercapto)-2-pyrimidinone 在 氨 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以95%的产率得到1-(2-deoxy-α-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone
  参考文献：
  名称：

  Synthesis and antiviral activity of 1-(2-deoxy-.beta.-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone

  摘要：

  1-(2-Deoxy-beta-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone (1b) was synthesized via modification of the silyl method. 1b inhibits the Herpes simplex virus type 1 (98%) and type 2 (97%) at a concentration which is nontoxic to human HeLa cells. The compound shows 50 times greater binding affinity (lower Ki) to the virus-specific thymidine kinase than to the thymidine kinase of uninfected HeLa cells.

  DOI：

  10.1021/jm00133a022

文献信息

• Synthesis and antiviral activity of 1-(2-deoxy-.beta.-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone
  作者：Alan C. Schroeder、Thomas J. Bardos、Yung-Chi Cheng

  DOI：10.1021/jm00133a022

  日期：1981.1

  1-(2-Deoxy-beta-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone (1b) was synthesized via modification of the silyl method. 1b inhibits the Herpes simplex virus type 1 (98%) and type 2 (97%) at a concentration which is nontoxic to human HeLa cells. The compound shows 50 times greater binding affinity (lower Ki) to the virus-specific thymidine kinase than to the thymidine kinase of uninfected HeLa cells.