Phenolic imidazole derivatives with dual antioxidant/antifungal activity: synthesis and structure-sctivity relationship
| Autor: | Maria João Sousa, Filipe Areias, Maria Fernanda Proença, João Pedro Silva, Francisco M. Fernandes, Marián Castro, Ana Paula Bettencourt, Olga P. Coutinho |
|---|---|
| Přispěvatelé: | Universidade do Minho |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Antifungal
Models Molecular Antioxidant Ciências Químicas [Ciências Naturais] Saúde de qualidade Stereochemistry medicine.drug_class Cell Survival medicine.medical_treatment Molecular Conformation Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Antioxidants Cell Line Phenolic imidazoles chemistry.chemical_compound Anti-Infective Agents Phenols Antioxidant activity Drug Discovery medicine Imidazole Structure–activity relationship Animals cancer Antifungal activity Science & Technology 010405 organic chemistry Imidazoles Structure-activity relationship Ciências Naturais::Ciências Químicas 0104 chemical sciences 3. Good health chemistry Phenolic purines |
| Zdroj: | Repositório Científico de Acesso Aberto de Portugal Repositório Científico de Acesso Aberto de Portugal (RCAAP) instacron:RCAAP |
| Popis: | Background: Previous publications show that the addition of a phenolic antioxidant to an antifungal agent, considerably enhances the antifungal activity. Objective: Synthesis of novel compounds combining phenolic units with linear or cyclic nitrogencontaining organic molecules with antioxidant/antifungal activity using methodologies previously developed in the group. Methods: Several N- [1,2-dicyano-2- (arylidenamino) vinyl]-O-alkylformamidoximes 3 were synthesized and cyclized to 4,5-dicyano-N- (N´-alcoxyformimidoyl)-2-arylimidazoles 4 upon reflux in DMF, in the presence of manganese dioxide or to 6-cyano-8-arylpurines 5 when the reagent was refluxed in acetonitrile with an excess of triethylamine. These compounds were tested for their antioxidant activity by cyclic voltammetry, DPPH radical (DPPH•) assay and deoxyribose degradation assay. The minimum inhibitory concentration (MIC) of all compounds was evaluated against two yeast species, Saccharomyces cerevisiae and Candida albicans, and against bacteria Bacillus subtilis (Gram-positive) and Escherichia coli (Gram negative). Their cytotoxicity was evaluated in fibroblasts. Results: Among the synthetised compounds, five presented higher antioxidant activity than reference antioxidant Trolox and from these compounds, four presented antifungal activity without toxic effects in fibroblasts and bacteria. Conclusion: Four novel compounds presented dual antioxidant/antifungal activity at concentrations that are not toxic to bacteria and fibroblasts. The active molecules can be used as an inspiration for further studies in this area. Fundação para a Ciência e Tecnologia (PPCDT/QUI/59356/2004). Fundação para a Ciência e Tecnologia (SFRH/BPD/26106/2005) |
| Databáze: | OpenAIRE |
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