Synthesis, Structures and Antifungal Activity of Selenoglycolurils

A synthetic method for the preparation of selenoglycolurils is reported. Target compounds were obtained by two‐stage transformation of unsubstituted, 1‐substituted and 1,3‐disubstituted thioglycolurils by S‐methylation with MeI to the corresponding isothiouronium salts (Step 1) followed by selenatio...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2023-04, Vol.8 (14), p.n/a
Main Authors: Galochkin, Anton A., Baranov, Vladimir V., Hansford, Karl A., Friberg, Louise I. M., Strel'tzova, Elena D., Lipatov, Egor S., Nelyubina, Yulia V., Kravchenko, Angelina N.
Format: Article
Language:English
Subjects:
Antifungals
Candida albicans
Cryptococcus neoformans
Organoselenium compounds
Thioglycoluril
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Summary:A synthetic method for the preparation of selenoglycolurils is reported. Target compounds were obtained by two‐stage transformation of unsubstituted, 1‐substituted and 1,3‐disubstituted thioglycolurils by S‐methylation with MeI to the corresponding isothiouronium salts (Step 1) followed by selenation with NaHSe generated in situ from grey Se and NaBH4 (Step 2). Selenoglycolurils possessed potent antifungal activity against Candida albicans and Cryptococcus neoformans (MIC 0.25–0.125 μg/mL) with no discernable toxicity against mamallian cells, supporting the unique role of organoselenium compounds as novel antifungal agents. Here we disclosed an easy‐to‐perform two‐step synthetic route to a new class of compounds ‐ selenoglycolurils ‐ with potent antifungal activity against Candida albicans and Cryptococcus neoformans. Compounds obtained show no discernable toxicity against mamallian cells, supporting the unique role of organoselenium compounds as novel antifungal agents.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202300765