Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Autores: Aguilar Llanos, Esteban; Carrera Pacheco, Saskya E.; González Pastor, Rebeca; Zúñiga Miranda, Johana; Rodríguez Pólit, Cristina; Mayorga Ramos, Arianna; Carrillo Naranjo, Oscar; Guamán, Linda P.; Romero Benavides, Juan Carlos; Cevallos Morillo, Carlos; Echeverría, Gustavo A.; Piro, Oscar Enrique; Alcívar León, Christian David; Heredia Moya, Jorge
Año de publicación: 2023
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet-vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound’s molecular properties, UV-vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C-N and C-C σ-bonds. Furthermore, as a result of extended bonding, the > C═N- azomethine group-containing Cpyr-N═(CH)-(CR)═(CH)-Cbz chain (with R═H for 3b, 3d, and 3h, and R═CH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C-H···O and C-H···N hydrogen bonds, π···π stacking, and C-H···π and C═O···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations.
Fil: Aguilar Llanos, Esteban. Universidad Central del Ecuador; Ecuador
Fil: Carrera Pacheco, Saskya E.. Universidad Ute; Ecuador
Fil: González Pastor, Rebeca. Universidad Ute; Ecuador
Fil: Zúñiga Miranda, Johana. Universidad Ute; Ecuador
Fil: Rodríguez Pólit, Cristina. Universidad Ute; Ecuador
Fil: Mayorga Ramos, Arianna. Universidad Ute; Ecuador
Fil: Carrillo Naranjo, Oscar. Universidad Ute; Ecuador
Fil: Guamán, Linda P.. Universidad Ute; Ecuador
Fil: Romero Benavides, Juan Carlos. Universidad Técnica Particular de Loja; Ecuador
Fil: Cevallos Morillo, Carlos. Universidad Central del Ecuador; Ecuador
Fil: Echeverría, Gustavo A.. 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. 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: Alcívar León, Christian David. Universidad Central del Ecuador; Ecuador. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Heredia Moya, Jorge. Universidad Ute; Ecuador
Materia: Schiﬀ base derivatives
Intermolecular Interactions
X-ray diffraction
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/243186

Acceder

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repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-AminoantipyrineAguilar Llanos, EstebanCarrera Pacheco, Saskya E.González Pastor, RebecaZúñiga Miranda, JohanaRodríguez Pólit, CristinaMayorga Ramos, AriannaCarrillo Naranjo, OscarGuamán, Linda P.Romero Benavides, Juan CarlosCevallos Morillo, CarlosEcheverría, Gustavo A.Piro, Oscar EnriqueAlcívar León, Christian DavidHeredia Moya, JorgeSchiﬀ base derivativesIntermolecular InteractionsX-ray diffractionhttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet-vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound’s molecular properties, UV-vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C-N and C-C σ-bonds. Furthermore, as a result of extended bonding, the > C═N- azomethine group-containing Cpyr-N═(CH)-(CR)═(CH)-Cbz chain (with R═H for 3b, 3d, and 3h, and R═CH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C-H···O and C-H···N hydrogen bonds, π···π stacking, and C-H···π and C═O···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations.Fil: Aguilar Llanos, Esteban. Universidad Central del Ecuador; EcuadorFil: Carrera Pacheco, Saskya E.. Universidad Ute; EcuadorFil: González Pastor, Rebeca. Universidad Ute; EcuadorFil: Zúñiga Miranda, Johana. Universidad Ute; EcuadorFil: Rodríguez Pólit, Cristina. Universidad Ute; EcuadorFil: Mayorga Ramos, Arianna. Universidad Ute; EcuadorFil: Carrillo Naranjo, Oscar. Universidad Ute; EcuadorFil: Guamán, Linda P.. Universidad Ute; EcuadorFil: Romero Benavides, Juan Carlos. Universidad Técnica Particular de Loja; EcuadorFil: Cevallos Morillo, Carlos. Universidad Central del Ecuador; EcuadorFil: Echeverría, Gustavo A.. 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. 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: Alcívar León, Christian David. Universidad Central del Ecuador; Ecuador. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Heredia Moya, Jorge. Universidad Ute; EcuadorAmerican Chemical Society Inc2023-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/243186Aguilar Llanos, Esteban; Carrera Pacheco, Saskya E.; González Pastor, Rebeca; Zúñiga Miranda, Johana; Rodríguez Pólit, Cristina; et al.; Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine; American Chemical Society Inc; ACS Omega; 8; 45; 11-2023; 42632-426462470-1343CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.3c05372info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsomega.3c05372info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:30:50Zoai:ri.conicet.gov.ar:11336/243186instacron: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:34982025-10-22 11:30:50.87CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
title	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
spellingShingle	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine Aguilar Llanos, Esteban Schiﬀ base derivatives Intermolecular Interactions X-ray diffraction
title_short	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
title_full	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
title_fullStr	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
title_full_unstemmed	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
title_sort	Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine
dc.creator.none.fl_str_mv	Aguilar Llanos, Esteban Carrera Pacheco, Saskya E. González Pastor, Rebeca Zúñiga Miranda, Johana Rodríguez Pólit, Cristina Mayorga Ramos, Arianna Carrillo Naranjo, Oscar Guamán, Linda P. Romero Benavides, Juan Carlos Cevallos Morillo, Carlos Echeverría, Gustavo A. Piro, Oscar Enrique Alcívar León, Christian David Heredia Moya, Jorge
author	Aguilar Llanos, Esteban
author_facet	Aguilar Llanos, Esteban Carrera Pacheco, Saskya E. González Pastor, Rebeca Zúñiga Miranda, Johana Rodríguez Pólit, Cristina Mayorga Ramos, Arianna Carrillo Naranjo, Oscar Guamán, Linda P. Romero Benavides, Juan Carlos Cevallos Morillo, Carlos Echeverría, Gustavo A. Piro, Oscar Enrique Alcívar León, Christian David Heredia Moya, Jorge
author_role	author
author2	Carrera Pacheco, Saskya E. González Pastor, Rebeca Zúñiga Miranda, Johana Rodríguez Pólit, Cristina Mayorga Ramos, Arianna Carrillo Naranjo, Oscar Guamán, Linda P. Romero Benavides, Juan Carlos Cevallos Morillo, Carlos Echeverría, Gustavo A. Piro, Oscar Enrique Alcívar León, Christian David Heredia Moya, Jorge
author2_role	author author author author author author author author author author author author author
dc.subject.none.fl_str_mv	Schiﬀ base derivatives Intermolecular Interactions X-ray diffraction
topic	Schiﬀ base derivatives Intermolecular Interactions X-ray diffraction
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.3 https://purl.org/becyt/ford/1 https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet-vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound’s molecular properties, UV-vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C-N and C-C σ-bonds. Furthermore, as a result of extended bonding, the > C═N- azomethine group-containing Cpyr-N═(CH)-(CR)═(CH)-Cbz chain (with R═H for 3b, 3d, and 3h, and R═CH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C-H···O and C-H···N hydrogen bonds, π···π stacking, and C-H···π and C═O···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations. Fil: Aguilar Llanos, Esteban. Universidad Central del Ecuador; Ecuador Fil: Carrera Pacheco, Saskya E.. Universidad Ute; Ecuador Fil: González Pastor, Rebeca. Universidad Ute; Ecuador Fil: Zúñiga Miranda, Johana. Universidad Ute; Ecuador Fil: Rodríguez Pólit, Cristina. Universidad Ute; Ecuador Fil: Mayorga Ramos, Arianna. Universidad Ute; Ecuador Fil: Carrillo Naranjo, Oscar. Universidad Ute; Ecuador Fil: Guamán, Linda P.. Universidad Ute; Ecuador Fil: Romero Benavides, Juan Carlos. Universidad Técnica Particular de Loja; Ecuador Fil: Cevallos Morillo, Carlos. Universidad Central del Ecuador; Ecuador Fil: Echeverría, Gustavo A.. 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. 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: Alcívar León, Christian David. Universidad Central del Ecuador; Ecuador. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Heredia Moya, Jorge. Universidad Ute; Ecuador
description	Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet-vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound’s molecular properties, UV-vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C-N and C-C σ-bonds. Furthermore, as a result of extended bonding, the > C═N- azomethine group-containing Cpyr-N═(CH)-(CR)═(CH)-Cbz chain (with R═H for 3b, 3d, and 3h, and R═CH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C-H···O and C-H···N hydrogen bonds, π···π stacking, and C-H···π and C═O···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations.
publishDate	2023
dc.date.none.fl_str_mv	2023-11
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/11336/243186 Aguilar Llanos, Esteban; Carrera Pacheco, Saskya E.; González Pastor, Rebeca; Zúñiga Miranda, Johana; Rodríguez Pólit, Cristina; et al.; Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine; American Chemical Society Inc; ACS Omega; 8; 45; 11-2023; 42632-42646 2470-1343 CONICET Digital CONICET
url	http://hdl.handle.net/11336/243186
identifier_str_mv	Aguilar Llanos, Esteban; Carrera Pacheco, Saskya E.; González Pastor, Rebeca; Zúñiga Miranda, Johana; Rodríguez Pólit, Cristina; et al.; Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine; American Chemical Society Inc; ACS Omega; 8; 45; 11-2023; 42632-42646 2470-1343 CONICET Digital CONICET
dc.language.none.fl_str_mv	eng
language	eng
dc.relation.none.fl_str_mv	info:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.3c05372 info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsomega.3c05372
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	American Chemical Society Inc
publisher.none.fl_str_mv	American Chemical Society Inc
dc.source.none.fl_str_mv	reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str	CONICET Digital (CONICET)
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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	12.982451

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

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