5'-ethynyl-5'-deoxythymidine | 64189-24-8

• 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: 5'-ethynyl-5'-deoxythymidine
• 英文别名: 1-(5-ethynyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione；1-[(2R,4S,5R)-5-ethynyl-4-hydroxy-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5R)-5-ethynyl-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 64189-24-8
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: ZNNAPEIPLZMQPU-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-ethynyl-5'-deoxythymidine 在 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.58h， 生成 1-{N⁴-[3’-O-tert-butyl dimethylsilyl -5’-O-(4,4’-dimethoxytrityl)-2’-deoxy-5- methylcytidylyl]}-6-{N⁴-[1-(2,5,6-trideoxy-β-D-erythro-hex-5-ynofuranosyl)-5-methyl cytosinyl]}hexane
  参考文献：
  名称：

  A multifunctional toolkit for target-directed cancer therapy

  摘要：

  以单一结构编码多种功能的新型肿瘤靶向 RNA 工具包。

  DOI：

  10.1039/c8cc08823c

文献信息

• A new building block for DNA network formation by self-assembly and polymerase chain reaction
  作者：Holger Bußkamp、Sascha Keller、Marta Robotta、Malte Drescher、Andreas Marx

  DOI：10.3762/bjoc.10.104

  日期：——

  toolbox for many different manipulations to construct nanometer scaled objects. We present a straightforward synthesis of a rigid DNA branching building block successfully used for the generation of DNA networks by self-assembly and network formation by enzymatic DNA synthesis. The Y-shaped 3-armed DNA construct, bearing 3 primer strands is accepted by Taq DNA polymerase. The enzyme uses each arm as primer

  许多纳米技术方法都利用了 DNA 自组装的可预测性。受自然存在的自组装 DNA 结构的启发，分支 DNA 已被开发出来，允许自组装到具有纳米级尺寸的预先设计的结构。DNA 是一种用于生成纳米结构的有吸引力的材料，因为有大量的酶可以高精度地修饰 DNA，为构建纳米尺度物体的许多不同操作提供了一个工具箱。我们提出了一种直接合成的刚性 DNA 分支构建块，成功用于通过自组装和酶促 DNA 合成形成网络来生成 DNA 网络。带有 3 条引物链的 Y 形 3 臂 DNA 构建体被 Taq DNA 聚合酶接受。该酶使用每个臂作为引物链，并在 PCR 过程中将分支构建体整合到大型组件中。通过琼脂糖凝胶电泳、原子力显微镜、动态光散射和电子顺磁共振光谱研究网络。研究结果表明，形成了相当严格的 DNA 网络。这为 DNA 材料的形成提供了一种新的自下而上的方法，可能会在功能水凝胶的生成中找到应用。
• [EN] A COMPOUND COMPRISING RNA COMPOUNDS AND BCM MOIETIES<br/>[FR] COMPOSÉ COMPRENANT DES COMPOSÉS D'ARN ET DES FRACTIONS DE BCM
  申请人：FUNDACIO INST DE RECERCA BIOMEDICA IRB BARCELONA

  公开号：WO2019086437A1

  公开（公告）日：2019-05-09

  The invention refers to a compound comprising a compound A n, a compound B n and a compound C n, wherein A n comprises RNA compounds A Tn and A Bn and a first BCm moiety of the general formula (I) with the structure A Tn -BCm-A Bn, B n comprises RNA compounds B Bn and B Tn and a second BCm moiety, with the structure B Bn -BCm-B Tn, and C n comprises RNA compounds C Tn a and C Tn b, a third BCm moiety, with the structure C Tn b-BCm-C Tn a and a RNA compound C Bn. The compound is useful as a medicament in the treatment of cancer and in a method for monitoring biological processes in vitro or in vivo. The invention also refers to a pharmaceutical composition comprising the compound. In addition, the invention refers to the use of BCm moieties for increasing stability of the RNA structure of the compound.

  本发明涉及一种化合物，包括化合物An、化合物Bn和化合物Cn。其中，An包括RNA化合物ATn和ABn以及通式（I）的第一种BCm基团，其结构为ATn-BCm-ABn；Bn包括RNA化合物BBn和BTn以及第二种BCm基团，其结构为BBn-BCm-BTn；Cn包括RNA化合物CTna和CTnb、第三种BCm基团，其结构为CTnb-BCm-CTna以及RNA化合物CBn。该化合物在治疗癌症和监测体内或体外生物过程的方法中可用作药物。本发明还涉及一种包括该化合物的制药组合物。此外，本发明还涉及使用BCm基团来增加该化合物RNA结构稳定性的方法。
• Ligands for the affinity chromatography of mammalian thymidine kinase 1: Strategy, synthesis and evaluation
  作者：Rainer A. Beck、Birgitte Munch-Petersen、Michael Dölker、Lisbet Cloos、Gerda Tyrsted、Kurt Eger

  DOI：10.1016/s0031-6865(96)00029-5

  日期：1996.10

  Selected thymidine derivatives were synthesized with various spacers and fixed as model compounds at position N-3', C-5, C-3' and C-5', respectively, to simulate the preparation of an affinity gel matrix. Compounds 3, 6, 7 and 9 were evaluated for their effect on pure human cytosolic thymidine kinase (TK). All four compounds showed competitive inhibition with respect to thymidine, with Ki-values between 80 and 1000 microM. In the same positions as the model compounds were bound to the spacers thymidine derivatives were coupled with different Sepharose gel matrices. These affinity matrices were tested for isolation of thymidine kinase out of placental enzyme material. Except for one matrix, more than 98% of the applied activity was retained by the affinity matrices tested. The strongest binding to the enzyme resulted from a fixation at C-5' of the thymidine molecule to the gel matrix.
• A multifunctional toolkit for target-directed cancer therapy
  作者：Montserrat Terrazas、Dani Sánchez、Federica Battistini、Núria Villegas、Isabelle Brun-Heath、Modesto Orozco

  DOI：10.1039/c8cc08823c

  日期：——

  A novel tumor-targeted RNA toolkit encoding multiple functions in a single structure.

  以单一结构编码多种功能的新型肿瘤靶向 RNA 工具包。