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

DSpace/Manakin Repository

Show simple item record

dc.creator Illicachi, Luis Alberto
dc.creator Montalvo-Acosta, Joel José
dc.creator Insuasty, Alberto
dc.creator Quiroga, Jairo
dc.creator Abonia, Rodrigo
dc.creator Sortino, Maximiliano
dc.creator Zacchino, Susana
dc.creator Insuasty, Braulio
dc.date.accessioned 2020-12-18T15:25:02Z
dc.date.available 2020-12-18T15:25:02Z
dc.date.issued 2017-09-05
dc.identifier.issn 1420-3049 es
dc.identifier.uri http://hdl.handle.net/2133/19512
dc.description Novel (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.description Para 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.sponsorship Departamento Administrativo de Ciencia, Tecnología e Innovación (Colciencias) es
dc.description.sponsorship Universidad del Valle es
dc.description.sponsorship Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT): PICT 2014-117 es
dc.format application/pdf
dc.format.extent 1-20 es
dc.language.iso eng es
dc.publisher MDPI es
dc.rights openAccess es
dc.rights.uri https://creativecommons.org/licenses/by/4.0/ *
dc.subject Antifungal Activity es
dc.subject Cyclocondensation Reaction es
dc.subject Chalcones es
dc.subject N-aryl-2-pyrazolines es
dc.subject Density Functional Theory Calculations es
dc.subject DFT Calculations es
dc.title 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 es
dc.type article
dc.type artículo
dc.type publishedVersion
dc.rights.holder Universidad Nacional de Rosario es
dc.rights.holder Illicachi, Luis Alberto es
dc.rights.holder Montalvo-Acosta, Joel José es
dc.rights.holder Insuasty, Alberto es
dc.rights.holder Quiroga, Jairo es
dc.rights.holder Abonia, Rodrigo es
dc.rights.holder Sortino, Maximiliano es
dc.rights.holder Zacchino, Susana es
dc.rights.holder Insuasty, Braulio es
dc.relation.publisherversion https://doi.org/10.3390/molecules22091476 es
dc.relation.publisherversion https://www.mdpi.com/1420-3049/22/9/1476 es
dc.rights.text Attribution 4.0 International (CC BY 4.0) es
dc.citation.title Molecules es
dc.citation.volume 22(9) es
dc.description.fil Fil: 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.fil Fil: Montalvo-Acosta, Joel José. Institut de Science et d’Ingénierie Supramoléculaires. Laboratoire d’Ingénierie des Fonctions Moléculaires; France. es
dc.description.fil Fil: Insuasty, Alberto. Universidad del Norte. Departamento de Química y Biología; Colombia. es
dc.description.fil Fil: 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.fil Fil: 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.fil Fil: Sortino, Maximiliano. Universidad Nacional de Rosario. Facultad de Farmacia y Bioquímica. Área Farmacognosia; Argentina. es
dc.description.fil Fil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina. es
dc.description.fil Fil: Insuasty, Braulio. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia. es
dc.type.collection articulo
dc.type.version publishedVersion es


Files in this item

The following license files are associated with this item:

This item appears in the following Collection(s)

Show simple item record

openAccess Except where otherwise noted, this item's license is described as openAccess

My Account


Search DSpace


Browse