Synthesis, Structures and Antifungal Activity of Selenoglycolurils

Author:

Galochkin Anton A.1ORCID,Baranov Vladimir V.1ORCID,Hansford Karl A.2ORCID,Friberg Louise I. M.2ORCID,Strel'tzova Elena D.1,Lipatov Egor S.3ORCID,Nelyubina Yulia V.3ORCID,Kravchenko Angelina N.1ORCID

Affiliation:

1. N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky prosp. 119991 Moscow Russian Federation

2. Centre for Superbug Solutions Institute for Molecular Bioscience The University of Queensland St. Lucia Queensland 4072 Australia

3. A.N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences 28 Vavilova St. 119991 Moscow Russian Federation

Abstract

AbstractA 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.

Funder

Ministry of Science and Higher Education of the Russian Federation

Publisher

Wiley

Subject

General Chemistry

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