新型半乙烯基糖色素的合成及抗真菌性能研究。

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-06-21 DOI:10.1007/s11030-025-11243-1

Vladimir V Baranov, Anton A Galochkin, Vera A Alferova, Anton P Tyurin, Anna L Alekseenko, Sergei V Popkov, Sabrie M Shakir-Alieva, Yuri A Strelenko, Natalya G Kolotyrkina, Angelina N Kravchenko

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引用次数: 0

摘要

以一系列半基糖基化合物为基础，将其s甲基化成异硫脲盐，然后与Se和NaBH4原位生成的NaHSe相互作用，实现了1-烷基-4-甲基和1,3,4-三烷基取代半基糖基化合物的通用两段合成。所得到的半四烯糖基化合物被测试为抗菌剂，并表现出对丝状真菌的选择性抑制。与先前报道的类似物进行了广泛的比较，揭示了它们的抑菌方式，并强调了硒原子的位阻对抗真菌活性的显著影响。这些发现表明，半四烯糖醇可能具有一种新的抗真菌机制，值得对其分子靶点进行进一步的详细研究。此外，1,3,4-三烷基半四烯糖基化合物能有效抑制植物病原真菌的生长。

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Synthesis and antifungal properties of the new semiselenoglycolurils.

The universal two-stage synthesis of 1-alkyl-4-methyl- and 1,3,4-trialkylsubstituted semiselenoglycolurils was realized on the basis of a range of semithioglycolurils, which were S-methylated to isothiouronium salts, followed by the interaction of the salts with NaHSe generated in situ from Se and NaBH₄. The resulting semiselenoglycolurils were tested as antimicrobials and exhibited selective inhibition of filamentous fungi. A broad comparison with previously reported analogs revealed their fungistatic mode of action and highlighted the significant influence of steric hindrance of the selenium atom on antifungal activity. These findings suggest that semiselenoglycolurils may possess a novel antifungal mechanism, warranting further detailed investigation of their molecular targets. In addition, 1,3,4-trialkylsemiselenoglycolurils effectively inhibit the growth of phytopathogenic fungi.

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;