3'-O-Acetyl-5'-O-tosylthymidin | 75145-86-7

• 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: 3'-O-Acetyl-5'-O-tosylthymidin
• 英文别名: Tos(-5)2-deoxy-D-eryPenf3Ac(b)-thymin-1-yl；[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-3-yl] acetate
• CAS: 75145-86-7
• 化学式: C₁₉H₂₂N₂O₈S
• 分子量: 438.458
• InChiKey: GHJVZRAILPFSAM-GVDBMIGSSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-Acetyl-5'-O-tosylthymidin 在 ammonium hydroxide 、 sodium azide 、 苄基三乙基氯化铵 、 copper diacetate 、 sodium ascorbate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5’-deoxy-5’-(4’’-(α-hydroxy-3’’’-phenoxybenzyl)triazolo)thymidine
  参考文献：
  名称：

  α-羟基-1,2,3-三唑连接的唾液酸转移酶抑制剂的合成和对 ST3GAL1、ST6GAL1 和 ST8SIA2 的选择性评价

  摘要：

  基于我们之前对 1,2,3-三唑连接的唾液酸转移酶抑制剂的研究，我们提出了一系列新化合物的设计和合成，这些化合物改进了母体支架的药物相似性。此外，我们还使用 STs hST3GAL1 、 hST6GAL1 和 hST8SIA2 进行了初步 SAR 研究。这项工作为选择性 ST 抑制剂的设计提供了新的见解，特别是考虑了不同的核苷衍生物。

  DOI：

  10.1002/cmdc.202400088
• 作为产物：
  描述：

  3'-O-acetyl-2'-deoxy-5'-O-(dimethoxytrityl)thymidine 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 生成 3'-O-Acetyl-5'-O-tosylthymidin
  参考文献：
  名称：

  三唑基13α-雌激素-核苷生物共轭物的合成及生物学评价。

  摘要：

  通过应用铜催化的炔-叠氮化物点击反应（CuAAC）合成了13α-雌酮的2'-脱氧核苷共轭物。为了引入叠氮基，选择了核苷的5'-位和13α-雌酮的3-羟基上的炔丙基醚官能团。当核苷的3'-羟基被乙酰基保护并且5'-羟基通过甲苯磺酰叠氮化物交换法进行修饰时，我们的手中获得了最佳收率。受保护的5'-叠氮核苷和甾类炔烃之间单击反应的常用条件通过使用1.5当量的Cu（I）催化剂进行了轻微修饰。所有制备的缀合物均通过MTT分析法在体外评估，其针对一组人类粘附细胞系（HeLa，通过体外放射性底物孵育研究了MCF-7和A2780）以及新缀合物对人17β-羟基类固醇脱氢酶1（17β-HSD1）的潜在抑制活性。一些受保护的缀合物对一组人类粘附癌细胞系表现出中等的抗增殖特性（受保护的胞苷缀合物被证明是最有效的，IC50值为9μM）。胸苷偶联物显示出相当大的17β-HSD1抑制活性（IC50 = 19μM）。一些

  DOI：

  10.3390/molecules21091212

文献信息

• Efficient synthesis and antifungal investigation of nucleosides’ quaternaryammonium salt derivatives
  作者：Barbara DMOCHOWSKA、Lucyna PELLOWSKA-JANUSZEK、Justyna SAMASZKO-FIERTEK、Rafal SLUSARZ、Roland WAKIEC、Janusz MADAJ

  DOI：10.3906/kim-1808-34

  日期：——

  Quaternary ammonium salts are a group of compounds with diverse biological properties, the most important of which are their antiviral, antibacterial, and antifungal activities. The quaternization reactions of 5'-$O$-tosyl derivatives of uridine and thymidine with triethylamine, trimethylamine, 4-($N$,$N$-dimethylamino)pyridine, 2-methylpyridine, and pyridine are described in this article. Two of the synthesized compounds are exceptional because they are first of this type that demonstrate concentration-dependent antifungal in vitro activity against two species of the genus Candida in minimal YNB-SG medium. The experimental results have been extended by adding full atom molecular dynamics simulations and substrates and products energies evaluation.

  季铵盐是一类具有多种生物特性的化合物，其中最重要的特性是其抗病毒、抗菌和抗真菌活性。本文描述了5'-$O$-托磺酸衍生物与三乙胺、三甲胺、4-（$N$，$N$-二甲氨基）吡啶、2-甲基吡啶和吡啶的季铵化反应。合成的两种化合物具有特殊性，因为它们是首次展示出在最小YNB-SG培养基中对真菌属Candida两种物种表现出浓度依赖性抗真菌体外活性的此类化合物。实验结果通过添加全原子分子动力学模拟和底物及产物能量评估得到了扩展。
• Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity
  作者：Subhra Prakash Chakrabarty、Ramesh Ramapanicker、Roli Mishra、Srinivasan Chandrasekaran、Hemalatha Balaram

  DOI：10.1016/j.bmc.2009.10.003

  日期：2009.12

  Sirtuins are NAD(+) dependent deacetylases that modulate various essential cellular functions. Development of peptide based inhibitors of Sir2s would prove useful both as pharmaceutical agents and as effectors by which downstream cellular alterations can be monitored. Click chemistry that utilizes Huisgen's 1,3-dipolar cycloaddition permits attachment of novel modifications onto the side chain of lysine. Herein, we report the synthesis of peptide analogues prepared using click reactions on N epsilon-propargyloxycarbonyl protected lysine residues and their characterization as inhibitors of Plasmodium falciparum Sir2 activity. The peptide based inhibitors exhibited parabolic competitive inhibition with respect to acetylated-peptide substrate and parabolic non-competitive inhibition with NAD(+) supporting the formation of EI2 and E.NAD(+).I-2 complexes. Cross-competition inhibition analysis with the non-competitive inhibitor nicotinamide (NAM) ruled out the possibility of the NAM-binding site being the second inhibitor binding site, suggesting the presence of a unique alternate pocket accommodating the inhibitor. One of these compounds was also found to be a potent inhibitor of the intraerythrocytic growth of P. falciparum with 50% inhibitory concentration in the micromolar range. (C) 2009 Elsevier Ltd. All rights reserved.
• Liu, Xiaohai; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1685 - 1694
  作者：Liu, Xiaohai、Reese, Colin B.

  DOI：——

  日期：——
• Novel chalcogenides of thymidine and uridine: synthesis, properties and applications
  作者：Kirubakaran Sivapriya、Perumal Suguna、S. Shubashree、Perali Ramu Sridhar、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2007.02.035

  日期：2007.7

  A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides. (C) 2007 Elsevier Ltd. All rights reserved.
• Meyer, Wilfried; Frollmann, Hartmut, Chemische Berichte, 1980, vol. 113, # 7, p. 2530 - 2544
  作者：Meyer, Wilfried、Frollmann, Hartmut

  DOI：——

  日期：——