1-(5-O-acetyl-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-4-thiothymine | 127825-33-6

• 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-(5-O-acetyl-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-4-thiothymine
• 英文别名: 1-(5-O-Acetyl-2,3-dideoxy-3-fluoro-beta-D-ribofuranosyl)-4-thiothymine；[(2R,3S,5R)-3-fluoro-5-(5-methyl-2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 127825-33-6
• 化学式: C₁₂H₁₅FN₂O₄S
• 分子量: 302.327
• InChiKey: XWAYCAQJNJGTHQ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-O-acetyl-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-4-thiothymine 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98 mg的产率得到3'-deoxy-3'-fluoro-4-thiothymidine
  参考文献：
  名称：

  Thiated derivatives of 2′,3′-dideoxy-3′-fluorothymidine: Synthesis, in vitro anti-HIV-1 activity and interaction with recombinant drug resistant HIV-1 reverse transcriptase forms

  摘要：

  Various thiated analogues of thymine 2',3'-dideoxy-3'-fluoronucleoside (FLT) and their 5'-monophosphates and 5'-triphosphates were prepared with the use of modified multistep procedures. The thiated analogues of FLT and FLTMP were evaluated against the wild type and drug- and multidrug-resistant strains of HIV-1, using the replicative phenotyping format of the deCIPhR assay, and showed potent inhibition of drug-resistant HIV-1 strains at low cytotoxicity. Additionally, inhibition of recombinant drug resistant forms of reverse transcriptase from single and multiple HIV-1 mutants by the synthesized 5'-triphosphates was investigated. The strongest inhibition was observed for K103N and Delta 67 mutants and the most potent anti-HIV-1 activity against drug resistant strains and the lowest cytotoxicity was exerted by S(4)FLTMP and FLTMP which may be regarded as potential anti-HIV/AIDS agents. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2011.05.012
• 作为产物：
  描述：

  5'-O-Acetyl-3'-fluorothymidine 在 diphosphorus pentasulfide 作用下， 以 吡啶 为溶剂， 生成 1-(5-O-acetyl-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-4-thiothymine
  参考文献：
  名称：

  2',3'-dideoxynucleoside pyrimidine compounds and carbocyclic analogs

  摘要：

  本发明揭示了具有抗病毒活性的2'，3'-二去氧核苷嘧啶化合物和2-硫代胸腺嘧啶环烷衍生物。这些化合物预计会表现出与2'，3'-二去氧核苷化合物及其类似物所认可的抗病毒活性相同的效果。

  公开号：

  US05496935A1

文献信息

• US5496935A
  申请人：——

  公开号：US5496935A

  公开（公告）日：1996-03-05