1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-(2,2,2-trifluoro-ethyl)-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: 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-(2,2,2-trifluoro-ethyl)-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-(2,2,2-trifluoroethyl)pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-(2,2,2-trifluoroethyl)pyrimidine-2,4-dione
• 化学式: C₁₁H₁₃F₃N₂O₄S
• 分子量: 326.296
• InChiKey: PUZKEWARCWLCTF-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3S)-2-acetoxymethyl-5-[2,4-dioxo-5-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-thiophen-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-(2,2,2-trifluoro-ethyl)-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

文献信息

• Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides
  作者：S. George Rahim、Naimisha Trivedi、Mirjana V. Bogunovic-Batchelor、George W. Hardy、Gail Mills、John W. T. Selway、Wendy Snowden、Edward Littler、Paul L. Coe、Ivan Basnak、Robert F. Whale、Richard T. Walker

  DOI：10.1021/jm950029r

  日期：1996.1.1

  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.