Synthesis and DFT calculations of novel vanillin-chalcones and their 3-aryl-5-(4-(2- (dimethylamino)- ethoxy)-3-methoxyphenyl)- 4,5-dihydro-1H-pyrazole-1-carbaldehyde derivatives as antifungal agents

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dc.citation.titleMoleculeses
dc.citation.volume22(9)es
dc.creatorIllicachi, Luis Alberto
dc.creatorMontalvo-Acosta, Joel José
dc.creatorInsuasty, Alberto
dc.creatorQuiroga, Jairo
dc.creatorAbonia, Rodrigo
dc.creatorSortino, Maximiliano Andrés
dc.creatorZacchino, Susana
dc.creatorInsuasty, Braulio
dc.date.accessioned2020-12-18T15:25:02Z
dc.date.available2020-12-18T15:25:02Z
dc.date.issued2017-09-05
dc.descriptionNovel (E)-1-(aryl)-3-(4-(2-(dimethylamino)ethoxy)-3-methoxyphenyl) prop-2-en-1-ones 4 were synthesized by a Claisen-Schmidt reaction of 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde (2) with several acetophenone derivatives 3. Subsequently, cyclocondensation reactions of chalcones 4 with hydrazine hydrate afforded the new racemic 3-aryl-5-(4-(2- (dimethylamino)ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehydes 5 when the reaction was carried out in formic acid. The antifungal activity of both series of compounds against eight fungal species was determined. In general, chalcone derivatives 4 showed better activities than pyrazolines 5 against all tested fungi. None of the compounds 4a–g and 5a–g showed activity against the three Aspergillus spp. In contrast, most of the compounds 4 showed moderate to high activities against three dermatophytes (MICs 31.25–62.5 µg/mL), being 4a followed by 4c the most active structures. Interestingly, 4a and 4c possess fungicidal rather than fungistatic activities, with MFC values between 31.25 and 62.5 µg/mL. The comparison of the percentages of inhibition of C. neoformans by the most active compounds 4, allowed us to know the role played by the different substituents of the chalcones’ A-ring. Also the most anti-cryptococcal compounds 4a–c and 4g, were tested in a second panel of five clinical C. neoformans strains in order to have an overview of their inhibition capacity not only of standardized but also of clinical C. neoformans strains. DFT calculations showed that the electrophilicity is the main electronic property to explain the differences in antifungal activities for the synthesized chalcones and pyrazolines compounds. Furthermore, a quantitative reactivity analysis showed that electron-withdrawing substituted chalcones presented the higher electrophilic character and hence, the greater antifungal activities among compounds of series 4.es
dc.descriptionPara citar este articulo: Illicachi, L.A.; Montalvo-Acosta, J.J.; Insuasty, A.; Quiroga, J.; Abonia, R.; Sortino, M.; Zacchino, S.; Insuasty, B. Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents. Molecules 2017, 22, 1476.
dc.description.filFil: Illicachi, Luis Alberto. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.es
dc.description.filFil: Montalvo-Acosta, Joel José. Institut de Science et d’Ingénierie Supramoléculaires. Laboratoire d’Ingénierie des Fonctions Moléculaires; France.es
dc.description.filFil: Insuasty, Alberto. Universidad del Norte. Departamento de Química y Biología; Colombia.es
dc.description.filFil: Quiroga, Jairo. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.es
dc.description.filFil: Abonia, Rodrigo. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.es
dc.description.filFil: Sortino, Maximiliano. Universidad Nacional de Rosario. Facultad de Farmacia y Bioquímica. Área Farmacognosia; Argentina.es
dc.description.filFil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.es
dc.description.filFil: Insuasty, Braulio. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.es
dc.description.sponsorshipDepartamento Administrativo de Ciencia, Tecnología e Innovación (Colciencias)es
dc.description.sponsorshipUniversidad del Vallees
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica (ANPCyT): PICT 2014-117es
dc.formatapplication/pdf
dc.format.extent1-20es
dc.identifier.issn1420-3049es
dc.identifier.urihttp://hdl.handle.net/2133/19512
dc.language.isoenges
dc.publisherMDPIes
dc.relation.publisherversionhttps://doi.org/10.3390/molecules22091476es
dc.relation.publisherversionhttps://www.mdpi.com/1420-3049/22/9/1476es
dc.rightsopenAccesses
dc.rights.holderUniversidad Nacional de Rosarioes
dc.rights.holderIllicachi, Luis Albertoes
dc.rights.holderMontalvo-Acosta, Joel Josées
dc.rights.holderInsuasty, Albertoes
dc.rights.holderQuiroga, Jairoes
dc.rights.holderAbonia, Rodrigoes
dc.rights.holderSortino, Maximiliano Andrés es
dc.rights.holderZacchino, Susanaes
dc.rights.holderInsuasty, Braulioes
dc.rights.textAttribution 4.0 International (CC BY 4.0)es
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/*
dc.subjectAntifungal Activityes
dc.subjectCyclocondensation Reactiones
dc.subjectChalconeses
dc.subjectN-aryl-2-pyrazolineses
dc.subjectDensity Functional Theory Calculationses
dc.subjectDFT Calculationses
dc.titleSynthesis and DFT calculations of novel vanillin-chalcones and their 3-aryl-5-(4-(2- (dimethylamino)- ethoxy)-3-methoxyphenyl)- 4,5-dihydro-1H-pyrazole-1-carbaldehyde derivatives as antifungal agentses
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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