New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship

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-diph...

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Main Authors:	Ana Bettencourt, Marián Castro, João Silva, Francisco Fernandes, Olga Coutinho, M. João Sousa, M. Fernanda Proença, Filipe Areias
Format:	Article
Language:	English
Published:	MDPI AG 2018-10-01
Series:	Molecules
Subjects:	Imidazoles phenolic compounds antifungal activity MIC antioxidant capacity structure-activity relationship
Online Access:	http://www.mdpi.com/1420-3049/23/10/2530

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spelling	doaj-d0542d8b37f5466c8bad75f0c23d48b72020-11-24T21:07:28ZengMDPI AGMolecules1420-30492018-10-012310253010.3390/molecules23102530molecules23102530New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity RelationshipAna Bettencourt0Marián Castro1João Silva2Francisco Fernandes3Olga Coutinho4M. João Sousa5M. Fernanda Proença6Filipe Areias7Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, PortugalDepartment 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, SpainDepartment of Biology, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, PortugalDepartment of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, PortugalDepartment of Biology, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, PortugalDepartment of Biology, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, PortugalDepartment of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, PortugalDepartment of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, PortugalA 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.http://www.mdpi.com/1420-3049/23/10/2530Imidazolesphenolic compoundsantifungal activityMICantioxidant capacitystructure-activity relationship
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Ana Bettencourt Marián Castro João Silva Francisco Fernandes Olga Coutinho M. João Sousa M. Fernanda Proença Filipe Areias
spellingShingle	Ana Bettencourt Marián Castro João Silva Francisco Fernandes Olga Coutinho M. João Sousa M. Fernanda Proença Filipe Areias New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship Molecules Imidazoles phenolic compounds antifungal activity MIC antioxidant capacity structure-activity relationship
author_facet	Ana Bettencourt Marián Castro João Silva Francisco Fernandes Olga Coutinho M. João Sousa M. Fernanda Proença Filipe Areias
author_sort	Ana Bettencourt
title	New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship
title_short	New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship
title_full	New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship
title_fullStr	New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship
title_full_unstemmed	New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship
title_sort	new nitrogen compounds coupled to phenolic units with antioxidant and antifungal activities: synthesis and structure–activity relationship
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2018-10-01
description	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.
topic	Imidazoles phenolic compounds antifungal activity MIC antioxidant capacity structure-activity relationship
url	http://www.mdpi.com/1420-3049/23/10/2530
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New Nitrogen Compounds Coupled to Phenolic Units with Antioxidant and Antifungal Activities: Synthesis and Structure–Activity Relationship

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