5-(2,2-Dichloro-1-fluoro-vinyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5-(2,2-Dichloro-1-fluoro-vinyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione
• 英文别名: 5-(2,2-dichloro-1-fluoro-vinyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione；5-(2,2-dichloro-1-fluoroethenyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₁₁H₁₁Cl₂FN₂O₄S
• 分子量: 357.19
• InChiKey: MHRRXVDFIDEAGA-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-(2,2-dichloro-1-fluoro-vinyl)-1H-pyrimidine-2,4-dione 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 5-(2,2-Dichloro-1-fluoro-vinyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r