Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone

Autores
Jios, Eliana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Ulic, Sonia Elizabeth; Viola, Carolina Maria; Arena, Mario Eduardo
Año de publicación
2025
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
(Z)-3-butylamino-4,4,4-trifluoro-1-(2-hydroxyphenyl)but-2-en-1-one (1), a new β-aminoenone, has been investigated in terms of its intra- and intermolecular interactions. Vibrational, electronic and nuclear magnetic resonance spectroscopies were used for the characterization,while X-ray diffraction methods afforded the determination of the crystal structure. The compound is arranged in the crystal lattice as centre-symmetric H-bonded dimeric aggregates (C2/c monoclinic space group). Both experimental (infrared, Raman, ultraviolet-visible transitions and X-ray diffraction data) and theoretical (Quantum Theory of Atoms in Molecules and Natural Bond Orbital approaches, calculated spectra and conformational analysis) methods were used to obtain a deep insight into the intra- and intermolecular contacts. The interactions were quali- and quantitatively analysed and the data compared with closely related compounds. In vitro experiments were carried out in this work to evaluate the antibacterial activity of 1 against Gram-positive and Gram-negative bacteria, particularly Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (6538).Compound 1 demonstrated a discernible suppression of biofilm formation and quorum sensing of both bacterial strains, indicating that it may be developed as an antibacterial candidate to reduce bacterial resistance and persistence on surfaces across a range of industries.
Fil: Jios, Eliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Viola, Carolina Maria. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Fil: Arena, Mario Eduardo. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Materia
Synthesis
Structural Analysis
Molecular Interactions
Theoretical Calculations
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:11336/279846
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/279846
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐AminoenoneJios, ElianaEcheverría, Gustavo AlbertoPiro, Oscar EnriqueJios, Jorge LuisUlic, Sonia ElizabethViola, Carolina MariaArena, Mario EduardoSynthesisStructural AnalysisMolecular InteractionsTheoretical Calculationshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1(Z)-3-butylamino-4,4,4-trifluoro-1-(2-hydroxyphenyl)but-2-en-1-one (1), a new β-aminoenone, has been investigated in terms of its intra- and intermolecular interactions. Vibrational, electronic and nuclear magnetic resonance spectroscopies were used for the characterization,while X-ray diffraction methods afforded the determination of the crystal structure. The compound is arranged in the crystal lattice as centre-symmetric H-bonded dimeric aggregates (C2/c monoclinic space group). Both experimental (infrared, Raman, ultraviolet-visible transitions and X-ray diffraction data) and theoretical (Quantum Theory of Atoms in Molecules and Natural Bond Orbital approaches, calculated spectra and conformational analysis) methods were used to obtain a deep insight into the intra- and intermolecular contacts. The interactions were quali- and quantitatively analysed and the data compared with closely related compounds. In vitro experiments were carried out in this work to evaluate the antibacterial activity of 1 against Gram-positive and Gram-negative bacteria, particularly Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (6538).Compound 1 demonstrated a discernible suppression of biofilm formation and quorum sensing of both bacterial strains, indicating that it may be developed as an antibacterial candidate to reduce bacterial resistance and persistence on surfaces across a range of industries.Fil: Jios, Eliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; ArgentinaFil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Viola, Carolina Maria. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; ArgentinaFil: Arena, Mario Eduardo. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; ArgentinaWiley VCH Verlag2025-02info: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/11336/279846Jios, Eliana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Ulic, Sonia Elizabeth; et al.; Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone; Wiley VCH Verlag; Chemistry and Biodiversity; 22; 6; 2-2025; 1-141612-1872CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/cbdv.202402089info:eu-repo/semantics/altIdentifier/doi/10.1002/cbdv.202402089info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-04-15T10:30:16Zoai:ri.conicet.gov.ar:11336/279846instacron: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:34982026-04-15 10:30:17.438CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
title Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
spellingShingle Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
Jios, Eliana
Synthesis
Structural Analysis
Molecular Interactions
Theoretical Calculations
title_short Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
title_full Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
title_fullStr Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
title_full_unstemmed Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
title_sort Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone
dc.creator.none.fl_str_mv Jios, Eliana
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
Viola, Carolina Maria
Arena, Mario Eduardo
author Jios, Eliana
author_facet Jios, Eliana
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
Viola, Carolina Maria
Arena, Mario Eduardo
author_role author
author2 Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
Viola, Carolina Maria
Arena, Mario Eduardo
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Synthesis
Structural Analysis
Molecular Interactions
Theoretical Calculations
topic Synthesis
Structural Analysis
Molecular Interactions
Theoretical Calculations
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv (Z)-3-butylamino-4,4,4-trifluoro-1-(2-hydroxyphenyl)but-2-en-1-one (1), a new β-aminoenone, has been investigated in terms of its intra- and intermolecular interactions. Vibrational, electronic and nuclear magnetic resonance spectroscopies were used for the characterization,while X-ray diffraction methods afforded the determination of the crystal structure. The compound is arranged in the crystal lattice as centre-symmetric H-bonded dimeric aggregates (C2/c monoclinic space group). Both experimental (infrared, Raman, ultraviolet-visible transitions and X-ray diffraction data) and theoretical (Quantum Theory of Atoms in Molecules and Natural Bond Orbital approaches, calculated spectra and conformational analysis) methods were used to obtain a deep insight into the intra- and intermolecular contacts. The interactions were quali- and quantitatively analysed and the data compared with closely related compounds. In vitro experiments were carried out in this work to evaluate the antibacterial activity of 1 against Gram-positive and Gram-negative bacteria, particularly Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (6538).Compound 1 demonstrated a discernible suppression of biofilm formation and quorum sensing of both bacterial strains, indicating that it may be developed as an antibacterial candidate to reduce bacterial resistance and persistence on surfaces across a range of industries.
Fil: Jios, Eliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Viola, Carolina Maria. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Fil: Arena, Mario Eduardo. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
description (Z)-3-butylamino-4,4,4-trifluoro-1-(2-hydroxyphenyl)but-2-en-1-one (1), a new β-aminoenone, has been investigated in terms of its intra- and intermolecular interactions. Vibrational, electronic and nuclear magnetic resonance spectroscopies were used for the characterization,while X-ray diffraction methods afforded the determination of the crystal structure. The compound is arranged in the crystal lattice as centre-symmetric H-bonded dimeric aggregates (C2/c monoclinic space group). Both experimental (infrared, Raman, ultraviolet-visible transitions and X-ray diffraction data) and theoretical (Quantum Theory of Atoms in Molecules and Natural Bond Orbital approaches, calculated spectra and conformational analysis) methods were used to obtain a deep insight into the intra- and intermolecular contacts. The interactions were quali- and quantitatively analysed and the data compared with closely related compounds. In vitro experiments were carried out in this work to evaluate the antibacterial activity of 1 against Gram-positive and Gram-negative bacteria, particularly Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (6538).Compound 1 demonstrated a discernible suppression of biofilm formation and quorum sensing of both bacterial strains, indicating that it may be developed as an antibacterial candidate to reduce bacterial resistance and persistence on surfaces across a range of industries.
publishDate 2025
dc.date.none.fl_str_mv 2025-02
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/11336/279846
Jios, Eliana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Ulic, Sonia Elizabeth; et al.; Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone; Wiley VCH Verlag; Chemistry and Biodiversity; 22; 6; 2-2025; 1-14
1612-1872
CONICET Digital
CONICET
url http://hdl.handle.net/11336/279846
identifier_str_mv Jios, Eliana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Ulic, Sonia Elizabeth; et al.; Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone; Wiley VCH Verlag; Chemistry and Biodiversity; 22; 6; 2-2025; 1-14
1612-1872
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://onlinelibrary.wiley.com/doi/10.1002/cbdv.202402089
info:eu-repo/semantics/altIdentifier/doi/10.1002/cbdv.202402089
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
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.203462

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