2',3'-didehydro-2',3'-dideoxythymidine-5'-yl H-phosphonate triethylammonium salt | 1419743-33-1

• 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: 2',3'-didehydro-2',3'-dideoxythymidine-5'-yl H-phosphonate triethylammonium salt
• 英文别名: triethylammonium 2',3'-didehydro-3'-deoxythymidin-5'-yl phosphonate
• CAS: 1419743-33-1
• 化学式: C₆H₁₅N*C₁₀H₁₃N₂O₆P
• 分子量: 389.389
• InChiKey: FZILIVBTCAILQL-KZYPOYLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113.86
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2',3'-didehydro-2',3'-dideoxythymidine-5'-yl H-phosphonate triethylammonium salt 在 吡啶 、 三甲基氯硅烷 、 碘 、 磷酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.18h， 以40%的产率得到
  参考文献：
  名称：

  从核苷 5'-H-膦酸酯单酯实际合成核苷 5'-二磷酸

  摘要：

  摘要 已经开发了一种基于 H-膦酸酯化学的简单方便的合成方案，用于制备核苷 5'-二磷酸。它包括在吡啶中用碘氧化甲硅烷基化的 H-膦酸酯单酯以产生相应的 N-吡啶鎓膦酸酯中间体，然后它们与用作亲核试剂的正磷酸反应。该方法的附加值是反应的底物 H-膦酸酯单酯可以由相应的核苷原位制备，无需分离即可用于下一步。该方法简单，适用于核糖和脱氧核糖核苷的各种二磷酸盐及其类似物的制备。图形概要

  DOI：

  10.1080/00397911.2020.1814817
• 作为产物：
  描述：

  司他夫定 在 吡啶 、 三甲基乙酰氯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2',3'-didehydro-2',3'-dideoxythymidine-5'-yl H-phosphonate triethylammonium salt
  参考文献：
  名称：

  3′-Modified oligodeoxyribonucleotides for the study of 2-deoxyribose damage in DNA

  摘要：

  Well-defined substrates for the study of oxidative processes are important for the elucidation of the role of DNA damage in the etiology of diseases such as cancer. We have synthesized 3'-modified oligodeoxyribonucleotides (ODNs) using 5' -> 3' 'reverse' DNA synthesis for the study of 2-deoxyribose oxidative damage to DNA. The modified monomers designed for these studies all share a common feature, they lack the naturally occurring 3'-hydroxyl group found in 2-deoxyribonucleosides. Modified H-phosphonates containing 3'-phenyl selenides as well as saturated and unsaturated sugars were obtained and incorporated in ODNs. These ODNs were used to investigate the fate of C3'-dideoxyribonucleotide radicals in DNA. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.050

文献信息

• An H-phosphonate strategy for the synthesis of 2′,3′-dideoxynucleoside triphosphates and homodinucleotides
  作者：Qi Sun、Si Liu、Jian Sun、Shan-Shan Gong

  DOI：10.1016/j.cclet.2013.11.029

  日期：2014.3
• Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2′,3′-dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity
  作者：Krystian Kolodziej、Joanna Romanowska、Jacek Stawinski、Jerzy Boryski、Aleksandra Dabrowska、Andrzej Lipniacki、Andrzej Piasek、Adam Kraszewski、Michal Sobkowski

  DOI：10.1016/j.ejmech.2015.06.004

  日期：2015.7

  Recently, AZT (N-pyridyl)phosphoramidates were reported as a new type of potential anti-HIV therapeutics. In continuation of that work, here we present new (N-heteroaryl)phosphoramidate derivatives of antiviral 2',3'-dideoxynucleosides containing other types of N-heteroaryl moieties, particularly those with higher lipophilicity. The present studies comprise mechanistic investigations using P-31 NMR correlation analysis, which permitted improvements in the synthetic procedures. The obtained compounds were tested in biological systems to establish their cytotoxicity and anti-HIV activity. The results were analyzed with respect to possible correlations between biological and physico-chemical properties of the phosphoramidates studied, to get some,insight into their antiviral mode of action. (C) 2015 Elsevier Masson SAS. All rights reserved.