Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates

Autores
Martín Acosta, Pedro; Peña, Rosalyn; Feresin, Gabriela Egly; Tapia, Alejandro; Lorenzo Castrillejo, Isabel; Machín, Félix; Amesty, Ángel; Estévez Braun, Ana
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities.
Fil: Martín Acosta, Pedro. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Fil: Peña, Rosalyn. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Juan; Argentina
Fil: Tapia, Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Lorenzo Castrillejo, Isabel. Hospital Universitario Nuestra Señora de la Candelaria; España. Universidad de La Laguna; España. Universidad Fernando Pessoa Canarias; España
Fil: Machín, Félix. Hospital Universitario Nuestra Señora de la Candelaria; España
Fil: Amesty, Ángel. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Fil: Estévez Braun, Ana. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Materia
ANTIMICROBIAL ACTIVITY
EMBELIN
MULTICOMPONENT REACTIONS
PRIVILEGED STRUCTURE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/152016
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/152016
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugatesMartín Acosta, PedroPeña, RosalynFeresin, Gabriela EglyTapia, AlejandroLorenzo Castrillejo, IsabelMachín, FélixAmesty, ÁngelEstévez Braun, AnaANTIMICROBIAL ACTIVITYEMBELINMULTICOMPONENT REACTIONSPRIVILEGED STRUCTUREhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities.Fil: Martín Acosta, Pedro. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaFil: Peña, Rosalyn. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaFil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Juan; ArgentinaFil: Tapia, Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Lorenzo Castrillejo, Isabel. Hospital Universitario Nuestra Señora de la Candelaria; España. Universidad de La Laguna; España. Universidad Fernando Pessoa Canarias; EspañaFil: Machín, Félix. Hospital Universitario Nuestra Señora de la Candelaria; EspañaFil: Amesty, Ángel. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaFil: Estévez Braun, Ana. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaMolecular Diversity Preservation International2020-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/152016Martín Acosta, Pedro; Peña, Rosalyn; Feresin, Gabriela Egly; Tapia, Alejandro; Lorenzo Castrillejo, Isabel; et al.; Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates; Molecular Diversity Preservation International; Molecules; 25; 14; 7-2020; 1-221420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/25/14/3290info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules25143290info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:49:25Zoai:ri.conicet.gov.ar:11336/152016instacron: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:34982025-10-15 14:49:25.916CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
title Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
spellingShingle Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
Martín Acosta, Pedro
ANTIMICROBIAL ACTIVITY
EMBELIN
MULTICOMPONENT REACTIONS
PRIVILEGED STRUCTURE
title_short Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
title_full Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
title_fullStr Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
title_full_unstemmed Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
title_sort Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates
dc.creator.none.fl_str_mv Martín Acosta, Pedro
Peña, Rosalyn
Feresin, Gabriela Egly
Tapia, Alejandro
Lorenzo Castrillejo, Isabel
Machín, Félix
Amesty, Ángel
Estévez Braun, Ana
author Martín Acosta, Pedro
author_facet Martín Acosta, Pedro
Peña, Rosalyn
Feresin, Gabriela Egly
Tapia, Alejandro
Lorenzo Castrillejo, Isabel
Machín, Félix
Amesty, Ángel
Estévez Braun, Ana
author_role author
author2 Peña, Rosalyn
Feresin, Gabriela Egly
Tapia, Alejandro
Lorenzo Castrillejo, Isabel
Machín, Félix
Amesty, Ángel
Estévez Braun, Ana
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIMICROBIAL ACTIVITY
EMBELIN
MULTICOMPONENT REACTIONS
PRIVILEGED STRUCTURE
topic ANTIMICROBIAL ACTIVITY
EMBELIN
MULTICOMPONENT REACTIONS
PRIVILEGED STRUCTURE
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 library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities.
Fil: Martín Acosta, Pedro. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Fil: Peña, Rosalyn. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Juan; Argentina
Fil: Tapia, Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Lorenzo Castrillejo, Isabel. Hospital Universitario Nuestra Señora de la Candelaria; España. Universidad de La Laguna; España. Universidad Fernando Pessoa Canarias; España
Fil: Machín, Félix. Hospital Universitario Nuestra Señora de la Candelaria; España
Fil: Amesty, Ángel. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
Fil: Estévez Braun, Ana. Universidad de La Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España
description A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities.
publishDate 2020
dc.date.none.fl_str_mv 2020-07
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/11336/152016
Martín Acosta, Pedro; Peña, Rosalyn; Feresin, Gabriela Egly; Tapia, Alejandro; Lorenzo Castrillejo, Isabel; et al.; Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates; Molecular Diversity Preservation International; Molecules; 25; 14; 7-2020; 1-22
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/152016
identifier_str_mv Martín Acosta, Pedro; Peña, Rosalyn; Feresin, Gabriela Egly; Tapia, Alejandro; Lorenzo Castrillejo, Isabel; et al.; Efficient multicomponent synthesis of diverse antibacterial embelin-privileged structure conjugates; Molecular Diversity Preservation International; Molecules; 25; 14; 7-2020; 1-22
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/url/https://www.mdpi.com/1420-3049/25/14/3290
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules25143290
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/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
_version_ 1846083016957362176
score 13.22299

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