3'-fluoro-3'-deoxythymidine-5'-O-β-triphosphate | 1314761-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-fluoro-3'-deoxythymidine-5'-O-β-triphosphate
• 英文别名: [(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl diphosphono phosphate
• CAS: 1314761-18-6
• 化学式: C₁₀H₁₆FN₂O₁₃P₃
• 分子量: 484.162
• InChiKey: XPYQLRPJNDECIR-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  219
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3’-脱氧-3-氟胸苷 在 C₁₅H₂₆N₄O₆P₃Pol 、 5-(乙硫基)-1H-四唑 、 叔丁基过氧化氢 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以85%的产率得到3'-fluoro-3'-deoxythymidine-5'-O-β-triphosphate
  参考文献：
  名称：

  Inhibition of multi-drug resistant HIV-1 reverse transcriptase by nucleoside β-triphosphates

  摘要：

  Despite the success of potent reverse transcriptase (RT) inhibitors against human immunodeficiency virus type 1 (HIV-1) in combination regimens, the development of drug resistant RTs constitutes a major hurdle for the long-term efficacy of current antiretroviral therapy. Nucleoside beta-triphosphate analogs of adenosine and nucleoside reverse transcriptase inhibitors (NRTIs) (3'-azido-2',3'-dideoxythymidine (AZT), 3'-fluoro-2',3'-dideoxythymidine (FLT), and 2',3'-didehydro-2',3'-dideoxythymidine (d4T)) were synthesized and their inhibitory activities were evaluated against wild-type and multidrug resistant HIV-1 RTs. Adenosine beta-triphosphate (1) and AZT beta-triphosphate (2) completely inhibited the DNA polymerase activity of wild type, the NRTI multi resistant, and nonnucleoside RT inhibitors (NNRTI) resistant HIV-1 RT at 10 nM, 10 and 100 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.005