1-[(2R,4S,5R)-5-[[4-[[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione | 1011727-49-3

• 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-[(2R,4S,5R)-5-[[4-[[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1011727-49-3
• 化学式: C₂₉H₄₃N₇O₉Si
• 分子量: 661.787
• InChiKey: UTRJBIUCJPZSJS-ZJCHSKCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[4-[[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1-[(2R,4S,5R)-4-hydroxy-5-[[4-[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  具有1,2,3-三唑键的核苷二聚体类似物：氟尿苷和胸苷的缀合为癌症治疗提供了新的工具。第二部分

  摘要：

  摘要具有1,2,3-三唑键的氟化核苷二聚体是生物有机化学领域中的新型化合物。我们报告了具有1,4-二取代的1,2,3-三唑键的不同排列的两组核苷二聚体类似物的合成和性质。基于对3JHH，3JH1'C2和3JH1'C6的分析，我们估计了糖部分的构象偏爱和糖苷键周围的方向。这些化合物显示出中等的抗癌活性，并在三种不同的癌细胞系中进行了细胞抑制研究。

  DOI：

  10.1080/15257770.2019.1610891
• 作为产物：
  描述：

  prop-2-ynyl(-3)[TBDMS(-5)]2-deoxy-Penf-thymin-1-yl 、 5-叠氮基-5-脱氧胸腺嘧啶脱氧核苷 在 L-ascorbic acid sodium salt 、 copper(II) sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.05h， 以80%的产率得到1-[(2R,4S,5R)-5-[[4-[[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Microwave-assisted synthesis of a triazole-linked 3′–5′ dithymidine using click chemistry

  摘要：

  Synthesis of a triazole-linked 3'-5' thymidine dimer making use of 1,3-dipolar cycloaddition is described. The azido-precursor was obtained by regioselective chlorination of thymidine, followed by azidation. The second precursor, a propargyl derivative, was obtained by selective 3'-O-alkylation of thymidine. Two 'click systems' were compared to obtain the desired dimer. These reactions were performed by microwave irradiation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.012

文献信息

• Microwave-assisted synthesis of a triazole-linked 3′–5′ dithymidine using click chemistry
  作者：Romain Lucas、Virginie Neto、Amel Hadj Bouazza、Rachida Zerrouki、Robert Granet、Pierre Krausz、Yves Champavier

  DOI：10.1016/j.tetlet.2007.12.012

  日期：2008.2

  Synthesis of a triazole-linked 3'-5' thymidine dimer making use of 1,3-dipolar cycloaddition is described. The azido-precursor was obtained by regioselective chlorination of thymidine, followed by azidation. The second precursor, a propargyl derivative, was obtained by selective 3'-O-alkylation of thymidine. Two 'click systems' were compared to obtain the desired dimer. These reactions were performed by microwave irradiation. (c) 2007 Elsevier Ltd. All rights reserved.
• Nucleoside dimers analogues with a 1,2,3-triazole linkage: conjugation of floxuridine and thymidine provides novel tools for cancer treatment. Part II
  作者：Dagmara Baraniak、Daniel Baranowski、Piotr Ruszkowski、Jerzy Boryski

  DOI：10.1080/15257770.2019.1610891

  日期：2019.11.2

  Abstract The fluorinated nucleoside dimers with a 1,2,3-triazole linkage are novel compounds within the field of bioorganic chemistry. We report on the synthesis and properties of two groups of nucleoside dimers analogs possessing a different arrangement of the 1,4-disubstituted 1,2,3-triazole linkage. Based on analysis of the 3JHH, 3JH1′C2, and 3JH1′C6 we estimated conformational preferences of sugar

  摘要具有1,2,3-三唑键的氟化核苷二聚体是生物有机化学领域中的新型化合物。我们报告了具有1,4-二取代的1,2,3-三唑键的不同排列的两组核苷二聚体类似物的合成和性质。基于对3JHH，3JH1'C2和3JH1'C6的分析，我们估计了糖部分的构象偏爱和糖苷键周围的方向。这些化合物显示出中等的抗癌活性，并在三种不同的癌细胞系中进行了细胞抑制研究。