Synthesis and antifungal properties of the new semiselenoglycolurils

Synthesis and antifungal properties of the new semiselenoglycolurils Full article

Journal

Molecular Diversity
ISSN: 1573-501X , E-ISSN: 1381-1991

Output data

Year: 2025, DOI: 10.1007/s11030-025-11243-1

Authors

Baranov Vladimir V ¹ , Galochkin Anton A ¹ , Alferova Vera A ^2,3 , Tyurin Anton P ^2,4 , Alekseenko Anna L ⁵ , Popkov Sergei V ⁵ , Shakir-Alieva Sabrie M ^2,3,5 , Strelenko Yuri A ¹ , Kolotyrkina Natalya G ¹ , Kravchenko Angelina N ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991, Moscow, Russian Federation. Ase1313@mail.ru.
2	Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, 16/10 Miklukho-Maklaya, 117997, Moscow, Russian Federation
3	Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Leninskye Gory, 1/40, 119991, Moscow, Russian Federation.
4	Chumakov Federal Scientific Center for Research and Development of Immune-and-Biological Products of Russian Academy of Sciences (Institute of Poliomyelitis), Village of Institute of Poliomyelitis, Settlement "Moskovskiy", 8/1, 108819, Moscow, Russian Federation.
5	Mendeleev University of Chemical Technology, 9 Miusskaya Sq., 125047, Moscow, Russian Federation.

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.

Baranov V.V. , Galochkin A.A. , Alferova V.A. , Tyurin A.P. , Alekseenko A.L. , Popkov S.V. , Shakir-Alieva S.M. , Strelenko Y.A. , Kolotyrkina N.G. , Kravchenko A.N.
Synthesis and antifungal properties of the new semiselenoglycolurils
Molecular Diversity. 2025. DOI: 10.1007/s11030-025-11243-1 WOS OpenAlex

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