New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship
Ana Bettencourt,
Marián Castro,
João Silva,
Francisco Fernandes,
Olga Coutinho,
M. João Sousa,
M. Fernanda Proença,
Filipe Areias
Affiliations
Ana Bettencourt
Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Marián Castro
Department of Pharmacology, Center for Research in Molecular Medicine and Chronic Diseases (CiMUS), Universidade de Santiago de Compostela, Avenida de Barcelona 22, 15782 Santiago de Compostela, Spain
João Silva
Department of Biology, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Francisco Fernandes
Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Olga Coutinho
Department of Biology, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
M. João Sousa
Department of Biology, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
M. Fernanda Proença
Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Filipe Areias
Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal
A selection of 1-amino-2-arylidenamine-1,2-(dicyano)ethenes 3 was synthesized and cyclized to 2-aryl-4,5-dicyano-1H-imidazoles 4 upon reflux in ethyl acetate/acetonitrile, in the presence of manganese dioxide. These compounds were tested for their antioxidant capacity by cyclic voltammetry, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and deoxyribose degradation assays. The minimum inhibitory concentration of all compounds was evaluated against two yeast species, Saccharomyces cerevisiae and Candida albicans. Their toxicity was tested in mammal fibroblasts. Among the synthesised compounds, two presented dual antioxidant/antifungal activity without toxic effects in fibroblasts. The new compounds synthesized in this work are potential biochemical tools and/or therapeutic drugs.
