Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxyge...

Autores
Ahmed, Muhammad Naeem; Arif, Muneeba; Andleeb, Hina; Ali Shah, Syed Wadood; Arshad, Ifzan; Tahir, Muhammad Nawaz; Rocha, Mariana; Gil, Diego Mauricio
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this study, three new hydrazide-based Schiff bases (1-3) have been synthesizedviasonication in good to excellent yields 73-90% and mainly characterized by UV-visible, IR,1H-NMR and single crystal X-ray diffraction analysis. The crystal structure of compounds1and2is stabilized by N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds, as well as C-H⋯π contacts. In addition, weak π⋯π stacking interactions were observed in the structure of2. A detailed analysis of the intermolecular interactions that stabilize the crystal packing has been performed by using Hirshfeld surface analysis and energy framework calculations were carried out to analyze and visualize the topology of the supramolecular assembly, indicating that the dispersion energy is dominant over the electrostatic one in the most energetic dimers of both compounds. The interaction energies associated with the noncovalent interactions observed in the crystal structures and the interplay between them have been calculated using DFT calculations. Moreover, these intermolecular interactions were also characterized by using both Bader´s quantum theory of atoms in molecules (QTAIM) and NCI plots. The synthesized alkoxybenzylidene analogs of benzohydrazide and acetohydrazide were screenedin vitroagainst soybean lipoxygenase and were found to show better activity than the standard indomethacin. Putative binding modes and comparison of binding interactions in the protein-ligand complex were analyzed by molecular docking studies.
Fil: Ahmed, Muhammad Naeem. University of Azad Jammu and Kashmir; Pakistán
Fil: Arif, Muneeba. University of Azad Jammu and Kashmir; Pakistán
Fil: Andleeb, Hina. Quaid-i-Azam University; Pakistán. International Islamic University Islamabad; Pakistán
Fil: Ali Shah, Syed Wadood. University of Malakand; Pakistán
Fil: Arshad, Ifzan. Quaid-i-Azam University; Pakistán
Fil: Tahir, Muhammad Nawaz. University of Sargodha; Pakistán
Fil: Rocha, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Gil, Diego Mauricio. 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Materia
SCHIFF BASES
NON CONVALENT INTERACTIONS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/148303
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/148303
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studiesAhmed, Muhammad NaeemArif, MuneebaAndleeb, HinaAli Shah, Syed WadoodArshad, IfzanTahir, Muhammad NawazRocha, MarianaGil, Diego MauricioSCHIFF BASESNON CONVALENT INTERACTIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this study, three new hydrazide-based Schiff bases (1-3) have been synthesizedviasonication in good to excellent yields 73-90% and mainly characterized by UV-visible, IR,1H-NMR and single crystal X-ray diffraction analysis. The crystal structure of compounds1and2is stabilized by N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds, as well as C-H⋯π contacts. In addition, weak π⋯π stacking interactions were observed in the structure of2. A detailed analysis of the intermolecular interactions that stabilize the crystal packing has been performed by using Hirshfeld surface analysis and energy framework calculations were carried out to analyze and visualize the topology of the supramolecular assembly, indicating that the dispersion energy is dominant over the electrostatic one in the most energetic dimers of both compounds. The interaction energies associated with the noncovalent interactions observed in the crystal structures and the interplay between them have been calculated using DFT calculations. Moreover, these intermolecular interactions were also characterized by using both Bader´s quantum theory of atoms in molecules (QTAIM) and NCI plots. The synthesized alkoxybenzylidene analogs of benzohydrazide and acetohydrazide were screenedin vitroagainst soybean lipoxygenase and were found to show better activity than the standard indomethacin. Putative binding modes and comparison of binding interactions in the protein-ligand complex were analyzed by molecular docking studies.Fil: Ahmed, Muhammad Naeem. University of Azad Jammu and Kashmir; PakistánFil: Arif, Muneeba. University of Azad Jammu and Kashmir; PakistánFil: Andleeb, Hina. Quaid-i-Azam University; Pakistán. International Islamic University Islamabad; PakistánFil: Ali Shah, Syed Wadood. University of Malakand; PakistánFil: Arshad, Ifzan. Quaid-i-Azam University; PakistánFil: Tahir, Muhammad Nawaz. University of Sargodha; PakistánFil: Rocha, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Gil, Diego Mauricio. 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaRoyal Society of Chemistry2021-01info: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/11336/148303Ahmed, Muhammad Naeem; Arif, Muneeba; Andleeb, Hina; Ali Shah, Syed Wadood; Arshad, Ifzan; et al.; Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies; Royal Society of Chemistry; CrystEngComm; 23; 4; 1-2021; 955-9711466-80331466-8033CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0CE01402Hinfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2021/CE/D0CE01402Hinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:56:38Zoai:ri.conicet.gov.ar:11336/148303instacron: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 11:56:38.827CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
title Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
spellingShingle Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
Ahmed, Muhammad Naeem
SCHIFF BASES
NON CONVALENT INTERACTIONS
title_short Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
title_full Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
title_fullStr Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
title_full_unstemmed Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
title_sort Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies
dc.creator.none.fl_str_mv Ahmed, Muhammad Naeem
Arif, Muneeba
Andleeb, Hina
Ali Shah, Syed Wadood
Arshad, Ifzan
Tahir, Muhammad Nawaz
Rocha, Mariana
Gil, Diego Mauricio
author Ahmed, Muhammad Naeem
author_facet Ahmed, Muhammad Naeem
Arif, Muneeba
Andleeb, Hina
Ali Shah, Syed Wadood
Arshad, Ifzan
Tahir, Muhammad Nawaz
Rocha, Mariana
Gil, Diego Mauricio
author_role author
author2 Arif, Muneeba
Andleeb, Hina
Ali Shah, Syed Wadood
Arshad, Ifzan
Tahir, Muhammad Nawaz
Rocha, Mariana
Gil, Diego Mauricio
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv SCHIFF BASES
NON CONVALENT INTERACTIONS
topic SCHIFF BASES
NON CONVALENT INTERACTIONS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this study, three new hydrazide-based Schiff bases (1-3) have been synthesizedviasonication in good to excellent yields 73-90% and mainly characterized by UV-visible, IR,1H-NMR and single crystal X-ray diffraction analysis. The crystal structure of compounds1and2is stabilized by N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds, as well as C-H⋯π contacts. In addition, weak π⋯π stacking interactions were observed in the structure of2. A detailed analysis of the intermolecular interactions that stabilize the crystal packing has been performed by using Hirshfeld surface analysis and energy framework calculations were carried out to analyze and visualize the topology of the supramolecular assembly, indicating that the dispersion energy is dominant over the electrostatic one in the most energetic dimers of both compounds. The interaction energies associated with the noncovalent interactions observed in the crystal structures and the interplay between them have been calculated using DFT calculations. Moreover, these intermolecular interactions were also characterized by using both Bader´s quantum theory of atoms in molecules (QTAIM) and NCI plots. The synthesized alkoxybenzylidene analogs of benzohydrazide and acetohydrazide were screenedin vitroagainst soybean lipoxygenase and were found to show better activity than the standard indomethacin. Putative binding modes and comparison of binding interactions in the protein-ligand complex were analyzed by molecular docking studies.
Fil: Ahmed, Muhammad Naeem. University of Azad Jammu and Kashmir; Pakistán
Fil: Arif, Muneeba. University of Azad Jammu and Kashmir; Pakistán
Fil: Andleeb, Hina. Quaid-i-Azam University; Pakistán. International Islamic University Islamabad; Pakistán
Fil: Ali Shah, Syed Wadood. University of Malakand; Pakistán
Fil: Arshad, Ifzan. Quaid-i-Azam University; Pakistán
Fil: Tahir, Muhammad Nawaz. University of Sargodha; Pakistán
Fil: Rocha, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Gil, Diego Mauricio. 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
description In this study, three new hydrazide-based Schiff bases (1-3) have been synthesizedviasonication in good to excellent yields 73-90% and mainly characterized by UV-visible, IR,1H-NMR and single crystal X-ray diffraction analysis. The crystal structure of compounds1and2is stabilized by N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds, as well as C-H⋯π contacts. In addition, weak π⋯π stacking interactions were observed in the structure of2. A detailed analysis of the intermolecular interactions that stabilize the crystal packing has been performed by using Hirshfeld surface analysis and energy framework calculations were carried out to analyze and visualize the topology of the supramolecular assembly, indicating that the dispersion energy is dominant over the electrostatic one in the most energetic dimers of both compounds. The interaction energies associated with the noncovalent interactions observed in the crystal structures and the interplay between them have been calculated using DFT calculations. Moreover, these intermolecular interactions were also characterized by using both Bader´s quantum theory of atoms in molecules (QTAIM) and NCI plots. The synthesized alkoxybenzylidene analogs of benzohydrazide and acetohydrazide were screenedin vitroagainst soybean lipoxygenase and were found to show better activity than the standard indomethacin. Putative binding modes and comparison of binding interactions in the protein-ligand complex were analyzed by molecular docking studies.
publishDate 2021
dc.date.none.fl_str_mv 2021-01
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/11336/148303
Ahmed, Muhammad Naeem; Arif, Muneeba; Andleeb, Hina; Ali Shah, Syed Wadood; Arshad, Ifzan; et al.; Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies; Royal Society of Chemistry; CrystEngComm; 23; 4; 1-2021; 955-971
1466-8033
1466-8033
CONICET Digital
CONICET
url http://hdl.handle.net/11336/148303
identifier_str_mv Ahmed, Muhammad Naeem; Arif, Muneeba; Andleeb, Hina; Ali Shah, Syed Wadood; Arshad, Ifzan; et al.; Interplay of weak noncovalent interactions in alkoxybenzylidene derivatives of benzohydrazide and acetohydrazide: a combined experimental and theoretical investigation and lipoxygenase inhibition (LOX) studies; Royal Society of Chemistry; CrystEngComm; 23; 4; 1-2021; 955-971
1466-8033
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/D0CE01402H
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2021/CE/D0CE01402H
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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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