3',5'-di-O-acetyl-4-thiothymidine | 20188-74-3

• 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: 3',5'-di-O-acetyl-4-thiothymidine
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-(5-methyl-2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 20188-74-3
• 化学式: C₁₄H₁₈N₂O₆S
• 分子量: 342.373
• InChiKey: XFOYEHUEGUDSJR-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-4-thiothymidine 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 4-硫代胸苷
  参考文献：
  名称：

  5-取代-4-硫代嘧啶核苷核磁共振谱的系统归属

  摘要：

  使用 NMR 光谱对 5-取代-4-硫代嘧啶核苷（核糖核苷和 2'-脱氧核苷）进行明确表征。5-溴-4-硫尿苷和相关核苷的所有质子和碳信号的分配是通过 COZY 和 HMQC 技术系统地进行并牢固建立的。比较了各种 4-硫代嘧啶核苷的 NMR 数据，并讨论了关键影响因素。这里介绍的方法适用于其他修饰的核苷和核苷酸，以及核碱基。版权所有 © 2013 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.3980
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 3',5'-di-O-acetyl-4-thiothymidine
  参考文献：
  名称：

  5-取代-4-硫代嘧啶核苷核磁共振谱的系统归属

  摘要：

  使用 NMR 光谱对 5-取代-4-硫代嘧啶核苷（核糖核苷和 2'-脱氧核苷）进行明确表征。5-溴-4-硫尿苷和相关核苷的所有质子和碳信号的分配是通过 COZY 和 HMQC 技术系统地进行并牢固建立的。比较了各种 4-硫代嘧啶核苷的 NMR 数据，并讨论了关键影响因素。这里介绍的方法适用于其他修饰的核苷和核苷酸，以及核碱基。版权所有 © 2013 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.3980

文献信息

• Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane
  作者：Raffaele Saladino、Enrico Mincione、Claudia Crestini、Maurizio Mezzetti

  DOI：10.1016/0040-4020(96)00289-x

  日期：1996.5

  and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings

  报道了通过用二甲基二环氧乙烷选择性氧化硫代核苷来合成几种嘧啶和嘌呤核苷的通用且方便的方法。嘧啶环的C-4位，嘌呤环的C-6和C-8位的Thioketo部分是氧化亲核取代的结构域。嘌呤和嘧啶环的C-2位的Thioketo部分是脱硫或二硫化物形成的区域。
• Ozonation of thionucleosides. A new chemical transformation of 4-thiouracil and 6-thioguanine nucleosides to cytosine and adenosine counterparts
  作者：Raffaele Saladino、Claudia Crestini、Francesca Occhionero、Rosario Nicoletti

  DOI：10.1016/0040-4020(95)00076-k

  日期：1995.3

  The ozonation of 4-thiopyrimidine and 6-thiopurine nucleosides in presence of amines afforded selectively and under mild experimental conditions several cytidine and adenosine nucleosides. The same reaction carried out in presence of alcohols afforded O4- or O6-alkylated derivatives of the nucleosides.

  在胺存在下对4-硫代嘧啶和6-硫代嘌呤核苷的臭氧化作用在温和的实验条件下选择性地提供了几个胞苷和腺苷核苷。在醇存在下进行相同的反应，得到核苷的O 4-或O 6-烷基化衍生物。
• 4-硫代脱氧胸苷衍生物及其抗乙肝病毒制药应用
  申请人：南京颐媛生物医学研究院有限公司

  公开号：CN113461760A

  公开（公告）日：2021-10-01

  本发明公开了4‑硫代脱氧胸苷衍生物及其抗乙肝病毒制药应用。本发明提供了4‑硫代脱氧胸苷衍生物或其药学上可接受的盐，其结构如结构式I或结构式II所示。本发明通过体外细胞毒性试验和体外抗HBV病毒药效试验，证实4‑硫代脱氧胸苷衍生物或其药学上可接受的盐具有抗HBV活性，具有抗乙肝药物开发前景，为治疗病毒性肝炎提供了一种潜在的选择。
• Saladino, Raffaele; Crestini, Claudia; Bernini, Roberta, Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3053 - 3054
  作者：Saladino, Raffaele、Crestini, Claudia、Bernini, Roberta、Frachey, Giuseppe、Mincione, Enrico

  DOI：——

  日期：——
• Exploring the binding of 4-thiothymidine with human serum albumin by spectroscopy, atomic force microscopy, and molecular modeling methods
  作者：Juling Zhang、Huaimin Gu、Xiaohui Zhang

  DOI：10.1016/j.carres.2013.11.018

  日期：2014.1

  The interaction of 4-thiothymidine (S(4)TdR) with human serum albumin (HSA) was studied by equilibrium dialysis under normal physiological conditions. In this work, the mechanism of the interaction between S(4)TdR and human serum albumin (HSA) was exploited by fluorescence, UV, CD circular, and SERS spectroscopic. Fluorescence and UV spectroscopy suggest that HSA intensities are significantly decreased when adding S(4)TdR to HAS, and the quenching mechanism of the fluorescence is static. Also, the DG, DH, and DS values across temperature indicated that hydrophobic interaction was the predominant binding force. The CD circular results show that there is little change in the secondary structure of HSA except the environment of amino acid changes when adding S(4)TdR to HSA. The surface-enhanced Raman scattering (SERS) shows that the interaction between S(4)TdR and HSA can be achieved through different binding sites which are probably located in the II A and III A hydrophobic pockets of HSA which correspond to Sudlow's I and II binding sites. In addition, the molecular modeling displays that S(4)TdR-HSA complex is stabilized by hydrophobic forces, which result from amino acid residues. The atomic force microscopy results revealed that the single HSA molecular dimensions were larger after interaction of 4-thiothymidine. This work would be useful to understand the state of the transportation, distribution, and metabolism of the anticancer drugs in the human body, and it could provide a useful biochemistry parameter for the development of new anti-cancer drugs and research of pharmacology mechanisms. (C) 2013 Elsevier Ltd. All rights reserved.