N-(3-propargyl)thymidine | 848349-53-1

• 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: N-(3-propargyl)thymidine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3-prop-2-ynylpyrimidine-2,4-dione
• CAS: 848349-53-1
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: LZHTUGCZNRVCGE-HBNTYKKESA-N

物化性质

• 熔点：
  87-88 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  485.2±55.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-propargyl)thymidine 在 4-二甲氨基吡啶 盐酸 、 sodium ascorbate 、 水 、 potassium carbonate 、 copper(II) sulfate 、 三乙胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 20.0~105.0 ℃ 、230.0 kPa 条件下， 反应 22.05h， 生成 (18)F-N3-((1-(2-fluoroethyl)-1H-[1,2,3]triazol-4-yl)methyl)thymidine
  参考文献：
  名称：

  WO2008/109080

  摘要：

  公开号：
• 作为产物：
  描述：

  1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3-(2-propynyl)thymine 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以97%的产率得到N-(3-propargyl)thymidine
  参考文献：
  名称：

  Triazole-Linked Dumbbell Oligodeoxynucleotides with NF-κB Binding Ability as Potential Decoy Molecules

  摘要：

  [Graphics]Triazole-cross-linked oligodeoxynucleotides were synthesized with use of the Cu(I) catalyzed alkyne-azide cycloaddition (CuAAC) with oligodeoxynucleotides possessing N-3-(azidoethyl)thymidine and N-3-(propargyl)thymidine at the 3'- and 5'-termini. The newly synthesized oligodeoxynucleotides were thermally stable and their global structures retained those of non-cross-linked oligodeoxynucleotides. The newly synthesized dumbbell oligodeoxynucleotides showed excellent stability against snake venom phosphodiesterase (3'-exonuclease) and high thermal stability, which are necessary for decoy molecules to achieve biological responses leading to alteration of gene expression. Moreover; dumbbell oligodeoxynucleotides have the ability to bind to NF-kappa B p50 homodimer within a similar range to that of a control double-stranded decoy olicodeoxynucleotide. This strategy allows us to prepare triazole-linked dumbbell oligodeoxynucleotides with a range of loop lengths, and we found that the greater the number of the thymidine residues constituting the loop region, the higher the binding affinity of the dumbbell oligodeoxynucleotides to the nuclear factor kappa B. This means that a protein binding ability of the dumbbell oligodeoxynucleotides could be modulated by altering the loop size. This study clearly shows that cross-linking by the triazole Structure does not prevent the dumbbell oligodeoxynucleotides from binding to the nuclear factor kappa B transcription factor. Therefore, the results obtained conclusively demonstrate that the triazole cross-linked dumbbell oligodeoxynucleotides could be proposed as powerful decoy molecules.

  DOI：

  10.1021/jo702459b

文献信息

• Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes
  作者：Anup M. Jawalekar、Erik Reubsaet、Floris P. J. T. Rutjes、Floris L. van Delft

  DOI：10.1039/c0cc04646a

  日期：——

  Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure mild enough to prepare a range of nucleoside and peptide conjugates. Exceptionally high reaction rates were found for the formation of 3,4,5-trisubstituted

  用高价碘处理肟可以通过迅速形成腈氧化物来生成取代的异恶唑。与末端炔烃的反应产生一系列具有完全区域选择性和高产率的3，5-二取代的异恶唑，该过程足够温和以制备一系列核苷和肽缀合物。发现由环状炔烃形成3,4,5-三取代异恶唑的反应速率极高。
• [EN] BOLA-AMPHIPHILIC COMPOUNDS AND THEIR USES FOR BIOMEDICAL APPLICATIONS<br/>[FR] COMPOSÉS BOLA-AMPHIPHILES ET LEURS UTILISATIONS POUR DES APPLICATIONS BIOMÉDICALES
  申请人：UNIV BORDEAUX

  公开号：WO2016055493A1

  公开（公告）日：2016-04-14

  The invention relates to bola-amphiphilic compounds and their uses for biomedical application. The invention particularly relates to the use of bola-amphiphilic compounds for providing low molecular weight gels (LMWG), useful, in particular, as culture media for animal or human cells, or as biocompatible material for biomedical applications.

  这项发明涉及到双链两性分子化合物及其在生物医学应用中的用途。该发明特别涉及双链两性分子化合物的应用，用于提供低分子量凝胶（LMWG），特别适用于作为动物或人类细胞的培养基，或作为生物医学应用的生物相容材料。
• Glycosyl–nucleoside–lipid based supramolecular assembly as a nanostructured material with nucleic acid delivery capabilities
  作者：Guilhem Godeau、Julie Bernard、Cathy Staedel、Philippe Barthélémy

  DOI：10.1039/b906212b

  日期：——

  A glycosyl–nucleoside–lipid self-assembles to give highly organized structures such as fibers and nanotubes, which can stabilize hydrogels; carbohydrate moieties provide a suitable environment to deliver nucleic acids into human cells.

  一种糖基-核苷酸-脂质自组装成高度有序的结构，如纤维和纳米管，这些结构能够稳定水凝胶；碳水化合物部分提供了一个适宜的环境，用于将核酸传递到人体细胞中。
• Supramolecular gels derived from nucleoside based bolaamphiphiles as a light-sensitive soft material
  作者：Julie Baillet、Alexandra Gaubert、Dario M. Bassani、Julien Verget、Laurent Latxague、Philippe Barthélémy

  DOI：10.1039/d0cc00336k

  日期：——

  Light-sensitive Low Molecular Weight Gelators (LMWGs) derived from glyconucleoside bolaamphiphiles containing a stilbene unit displayed gelation abilities in hydroalcoholic mixtures. These materials showed a gel-sol transition under UV irradiation thanks to E-Z isomerization of stilbene and could find potential applications as drug delivery systems.

  衍生自含有二苯乙烯单元的糖核苷类两亲物的光敏低分子量胶凝剂（LMWG）在水醇混合物中显示出胶凝能力。由于二苯乙烯的EZ异构化，这些材料在UV辐射下显示出凝胶-溶胶转变，并且可以发现其作为药物递送系统的潜在应用。
• [EN] NUCLEOSIDE ANALOGUES USEFUL AS POSITRON EMISSION TOMOGRAPHY (PET) IMAGING AGENTS<br/>[FR] ANALOGUES DE NUCLÉOSIDE UTILES EN TANT QU'AGENTS D'IMAGERIE DE TOMOGRAPHIE PAR ÉMISSION DE POSITONS (PET)
  申请人：IMP INNOVATIONS LTD

  公开号：WO2010023457A1

  公开（公告）日：2010-03-04

  The invention provides compounds that comprise a 4'-thio nucleoside that is a derivative of 4'-thiothymidine or 4'-thio-2'-deoxyuridine comprising a positron or single photon emitting radioisotope or corresponding non-radioactive isotope attached via a triazole link to the N-3 position. Methods for preparing such compounds and uses of the compounds in medicine are also provided.

  该发明提供了包含4'-硫代核苷的化合物，该核苷是4'-硫代胸苷或4'-硫代-2'-脱氧尿苷的衍生物，包括通过三唑键连接到N-3位置的正电子或单光子发射放射性同位素或相应的非放射性同位素。还提供了制备这种化合物的方法以及在医学上使用这些化合物的方法。