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
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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 Técnicas2025-09-29T10:01:18Zoai: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:34982025-09-29 10:01:19.206CONICET 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) |
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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1844613805512851456 |
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13.070432 |