Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity

Autores
Ferretti, Matías D.; Neto, Alexandre T.; Morel, Ademir F.; Kaufman, Teodoro Saul; Larghi, Enrique Leandro
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity.
Fil: Ferretti, Matías D.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Neto, Alexandre T.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; Brasil
Fil: Morel, Ademir F.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Materia
Bioactive Compounds
Novel Antibacterial Heterocycles
Broad Spectrum
3,3-Dibenzyl-4-Hydroxy-3,4-Dihydro-1h-Quinolin-2-Ones
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/5995
Acceder
id CONICETDig_f576ae679b61823e104decb3d35acf1a
oai_identifier_str oai:ri.conicet.gov.ar:11336/5995
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial ActivityFerretti, Matías D.Neto, Alexandre T.Morel, Ademir F.Kaufman, Teodoro SaulLarghi, Enrique LeandroBioactive CompoundsNovel Antibacterial HeterocyclesBroad Spectrum3,3-Dibenzyl-4-Hydroxy-3,4-Dihydro-1h-Quinolin-2-Oneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity.Fil: Ferretti, Matías D.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Neto, Alexandre T.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; BrasilFil: Morel, Ademir F.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaElsevier Masson2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5995Ferretti, Matías D.; Neto, Alexandre T.; Morel, Ademir F.; Kaufman, Teodoro Saul; Larghi, Enrique Leandro; Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity; Elsevier Masson; European Journal of Medical Chemistry; 81; 4-2014; 253-2560223-5234enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0223523414004383info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2014.05.024info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:22:21Zoai:ri.conicet.gov.ar:11336/5995instacron: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:34982025-09-10 13:22:21.203CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
title Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
spellingShingle Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
Ferretti, Matías D.
Bioactive Compounds
Novel Antibacterial Heterocycles
Broad Spectrum
3,3-Dibenzyl-4-Hydroxy-3,4-Dihydro-1h-Quinolin-2-Ones
title_short Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
title_full Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
title_fullStr Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
title_full_unstemmed Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
title_sort Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
dc.creator.none.fl_str_mv Ferretti, Matías D.
Neto, Alexandre T.
Morel, Ademir F.
Kaufman, Teodoro Saul
Larghi, Enrique Leandro
author Ferretti, Matías D.
author_facet Ferretti, Matías D.
Neto, Alexandre T.
Morel, Ademir F.
Kaufman, Teodoro Saul
Larghi, Enrique Leandro
author_role author
author2 Neto, Alexandre T.
Morel, Ademir F.
Kaufman, Teodoro Saul
Larghi, Enrique Leandro
author2_role author
author
author
author
dc.subject.none.fl_str_mv Bioactive Compounds
Novel Antibacterial Heterocycles
Broad Spectrum
3,3-Dibenzyl-4-Hydroxy-3,4-Dihydro-1h-Quinolin-2-Ones
topic Bioactive Compounds
Novel Antibacterial Heterocycles
Broad Spectrum
3,3-Dibenzyl-4-Hydroxy-3,4-Dihydro-1h-Quinolin-2-Ones
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity.
Fil: Ferretti, Matías D.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Neto, Alexandre T.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; Brasil
Fil: Morel, Ademir F.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
description A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity.
publishDate 2014
dc.date.none.fl_str_mv 2014-04
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/11336/5995
Ferretti, Matías D.; Neto, Alexandre T.; Morel, Ademir F.; Kaufman, Teodoro Saul; Larghi, Enrique Leandro; Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity; Elsevier Masson; European Journal of Medical Chemistry; 81; 4-2014; 253-256
0223-5234
url http://hdl.handle.net/11336/5995
identifier_str_mv Ferretti, Matías D.; Neto, Alexandre T.; Morel, Ademir F.; Kaufman, Teodoro Saul; Larghi, Enrique Leandro; Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity; Elsevier Masson; European Journal of Medical Chemistry; 81; 4-2014; 253-256
0223-5234
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0223523414004383
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2014.05.024
info:eu-repo/semantics/altIdentifier/doi/
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Masson
publisher.none.fl_str_mv Elsevier Masson
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 12.48226

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