Efficient synthesis, structure and anti-influenza virus activity of fluorinated pyrido[4,3-b][1,4]thiazine 1,1-dioxide derivatives

IF 1.7 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Fluorine Chemistry Pub Date : 2025-04-01 DOI:10.1016/j.jfluchem.2025.110430

Larisa Politanskaya , Bulat Khasanov , Irina Bagryanskaya , Maria Niukalova , Sergey Aksakov , Irina Balashova , Vladimir Zarubaev

引用次数: 0

Abstract

A series of fluorinated bicyclic fused compounds, containing fragments of pyridine and 3,4-dihydro-2H-1,4-thiazine 1,1-dioxide were synthesized via one-pot substitution of halogen atoms by N-nucleophiles in polyfluorinated precursor. Formation of the heterocyclic moiety was proceed as a two-stage process starting from Br replacement at the side chain followed by intramolecular aminodefluorination. The structures of some of the obtained heterocycles were confirmed using X-ray diffraction analysis. In addition, their inhibitory activity against influenza A/Puerto Rico/8/34 (H1N1) virus in MDCK cell culture was evaluated and compound-leader was found.

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氟化吡啶[4,3-b][1,4]噻嗪1,1-二衍生物的高效合成、结构及抗流感病毒活性

在多氟前驱体中，通过n -亲核试剂卤素原子的一锅取代，合成了一系列含吡啶和3,4-二氢- 2h -1,4-噻嗪1,1-二氧化基片段的氟化双环融合化合物。杂环部分的形成分为两个阶段，从侧链上的Br取代开始，然后是分子内的氨基脱氟。用x射线衍射分析证实了部分杂环的结构。此外，在MDCK细胞培养中测定了它们对甲型流感/波多黎各/8/34 （H1N1）病毒的抑制活性，并发现了化合物先导物。

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来源期刊

Journal of Fluorine Chemistry 化学-无机化学与核化学

CiteScore

3.80

自引率

10.50%

发文量

审稿时长

33 days

期刊介绍： The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.