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...

Autores
Illicachi, Luis Alberto; Montalvo Acosta, Joel José; Insuasty, Alberto; Quiroga, Jairo; Abonia, Rodrigo; Sortino, Maximiliano Andrés; Zacchino, Susana Alicia Stella; Insuasty, Braulio
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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-methoxy-benzaldehyde (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.
Fil: Illicachi, Luis Alberto. Universidad del Valle; Colombia
Fil: Montalvo Acosta, Joel José. Centre National de la Recherche Scientifique; Francia
Fil: Insuasty, Alberto. Universidad del Norte; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Materia
ANTIFUNGAL ACTIVITY
CHALCONES
CYCLOCONDENSATION REACTION
DFT CALCULATIONS
N-ARYL-2-PYRAZOLINES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/50662
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50662
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 agentsIllicachi, Luis AlbertoMontalvo Acosta, Joel JoséInsuasty, AlbertoQuiroga, JairoAbonia, RodrigoSortino, Maximiliano AndrésZacchino, Susana Alicia StellaInsuasty, BraulioANTIFUNGAL ACTIVITYCHALCONESCYCLOCONDENSATION REACTIONDFT CALCULATIONSN-ARYL-2-PYRAZOLINEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Novel (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-methoxy-benzaldehyde (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.Fil: Illicachi, Luis Alberto. Universidad del Valle; ColombiaFil: Montalvo Acosta, Joel José. Centre National de la Recherche Scientifique; FranciaFil: Insuasty, Alberto. Universidad del Norte; ColombiaFil: Quiroga, Jairo. Universidad del Valle; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Insuasty, Braulio. Universidad del Valle; ColombiaMolecular Diversity Preservation International2017-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/50662Illicachi, Luis Alberto; Montalvo Acosta, Joel José; Insuasty, Alberto; Quiroga, Jairo; Abonia, Rodrigo; et al.; 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; Molecular Diversity Preservation International; Molecules; 22; 9; 9-2017; 1-201420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/molecules22091476info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/22/9/1476info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:56:31Zoai:ri.conicet.gov.ar:11336/50662instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:56:32.081CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv 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
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
spellingShingle 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
Illicachi, Luis Alberto
ANTIFUNGAL ACTIVITY
CHALCONES
CYCLOCONDENSATION REACTION
DFT CALCULATIONS
N-ARYL-2-PYRAZOLINES
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
dc.creator.none.fl_str_mv Illicachi, Luis Alberto
Montalvo Acosta, Joel José
Insuasty, Alberto
Quiroga, Jairo
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Insuasty, Braulio
author Illicachi, Luis Alberto
author_facet Illicachi, Luis Alberto
Montalvo Acosta, Joel José
Insuasty, Alberto
Quiroga, Jairo
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Insuasty, Braulio
author_role author
author2 Montalvo Acosta, Joel José
Insuasty, Alberto
Quiroga, Jairo
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Insuasty, Braulio
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIFUNGAL ACTIVITY
CHALCONES
CYCLOCONDENSATION REACTION
DFT CALCULATIONS
N-ARYL-2-PYRAZOLINES
topic ANTIFUNGAL ACTIVITY
CHALCONES
CYCLOCONDENSATION REACTION
DFT CALCULATIONS
N-ARYL-2-PYRAZOLINES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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-methoxy-benzaldehyde (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.
Fil: Illicachi, Luis Alberto. Universidad del Valle; Colombia
Fil: Montalvo Acosta, Joel José. Centre National de la Recherche Scientifique; Francia
Fil: Insuasty, Alberto. Universidad del Norte; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
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-methoxy-benzaldehyde (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.
publishDate 2017
dc.date.none.fl_str_mv 2017-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/50662
Illicachi, Luis Alberto; Montalvo Acosta, Joel José; Insuasty, Alberto; Quiroga, Jairo; Abonia, Rodrigo; et al.; 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; Molecular Diversity Preservation International; Molecules; 22; 9; 9-2017; 1-20
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50662
identifier_str_mv Illicachi, Luis Alberto; Montalvo Acosta, Joel José; Insuasty, Alberto; Quiroga, Jairo; Abonia, Rodrigo; et al.; 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; Molecular Diversity Preservation International; Molecules; 22; 9; 9-2017; 1-20
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules22091476
info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/22/9/1476
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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