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 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 mu g/mL) with no discernable toxicity against mamallian cells, supporting the unique role of organoselenium compounds as novel antifungal agents.

Automated summary

A synthetic method for the preparation of selenoglycolurils was reported, where unsubstituted, 1-substituted, and 1,3-disubstituted thioglycolurils were transformed into isothiouronium salts through S-methylation with MeI (Step 1), followed by selenation with in situ generated NaHSe (Step 2). The selenoglycolurils showed potent antifungal activity against Candida albicans and Cryptococcus neoformans (MIC 0.25-0.125 μg/mL) without causing toxicity to mammalian cells, highlighting the unique role of organoselenium compounds as novel antifungal agents.