Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

Antonio Dell’Isola; Matthew M. W. McLachlan; Benjamin W. Neuman; Hawaa M. N. Al-Mullah; Alexander W. D. Binks; Warren Elvidge; Kenneth Shankland; Alexander J. A. Cobb

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Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

机译：螺环[1,2,3]-三唑恶嗪核苷的合成及抗病毒性能

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An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β-d-psicofuranose to the corresponding azido-derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3-dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.

机译：描述了螺环三唑恶嗪核苷的有效合成。这是通过将β-d-psicofuranose转化为相应的叠氮基衍生物，然后将伯醇与一系列通过Sonogashira化学方法获得的炔丙基溴烷基化来实现的。这些反应的产物平稳地进行1，3-偶极加成，生成受保护的螺环加合物。这些很容易脱保护得到相应的核糖核苷。使用MHV（小鼠肝炎病毒）作为模型研究了所得化合物库的抗病毒活性，其中衍生物3f显示出最有前途的活性和耐受性。

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《Chemistry: A European journal》 |2014年第37期|共5页
作者
Antonio Dell’Isola; Matthew M. W. McLachlan; Benjamin W. Neuman; Hawaa M. N. Al-Mullah; Alexander W. D. Binks; Warren Elvidge; Kenneth Shankland; Alexander J. A. Cobb;
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正文语种 eng
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关键词
alkynes; antiviral agents; cycloaddition; nucleosides; spiro compounds;

机译：炔烃;抗病毒药;环加成;核苷;螺化合物;

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1. Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides [J] . Antonio Dell’Isola, Matthew M. W. McLachlan, Benjamin W. Neuman, Chemistry: A European journal . 2014,第37期

机译：螺环[1,2,3]-三唑恶嗪核苷的合成及抗病毒性能
2. Synthesis and antiviral activity of novel spirocyclic nucleosides [J] . Cobb Alexander J. A., DellIsola Antonio, Abdulsattar Ban O., New Journal of Chemistry . 2018,第22期

机译：新型螺核苷的合成与抗病毒活性
3. Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs [J] . Maria de Lourdes G. Ferreira, Luiz C. S. Pinheiro, Osvaldo A. Santos-Filho, Medicinal chemistry research: an international journal for rapid communications on design and mechanisms of action of biologically active agents . 2014,第3期

机译：新的1H-1,2,3-三唑核苷利巴韦林类似物的设计，合成和抗病毒活性
4. Synthesis of Dinucleoside Triphosphates Containing Antiviral Nucleoside [C] . Rong LIU, Shan-Shan GONG International Conference on Biological Engineering and Pharmacy . 2017

机译：含有抗病毒核苷的二核苷三磷酸三磷酸酯的合成
5. I. Synthesis of saturated, DNA, and RNA spirocyclic-4,4-nonane nucleosides. II. Studies toward epoxy carbonate formation and the synthesis of suitable precursors. III. Methodological investigations involving the reactions of diazomethane with di-, tri-, and tetraketones. IV. Towards the total synthesis of salicifoline. [D] . Hartung, Ryan Eugene. 2005

机译：I.饱和，DNA和RNA螺环4，4-壬烷核苷的合成。二。研究环氧碳酸酯的形成和合适的前体的合成。三，方法学研究涉及重氮甲烷与二，三和四酮的反应。 IV。迈向水杨酸总合成。
6. Design synthesis antitubercular and antiviral properties of new spirocyclic indole derivatives [O] . Gökçe Cihan-Üstündağ, Lieve Naesens, Dilek Şatana, -1

机译：新螺环吲哚衍生物的设计合成抗结核和抗病毒特性
7. Synthesis and antiviral properties of spirocyclic 1,2,3-triazolooxazine nucleosides [O] . DellIsola Antonio, McLachlan Matthew M. W., Neuman Benjamin W., 2014

机译：螺环1,2,3-三唑恶嗪核苷的合成及抗病毒特性
8. Synthesis of Nucleoside Analogues with Potential Antiviral Activity against Negative Strand RNA Virus Targets. [R] . Walker, R. T. 1989

机译：具有抗负链RNa病毒靶标的潜在抗病毒活性的核苷类似物的合成。

Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

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