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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/148303
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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 Técnicas2025-09-29T10:23:52Zoai: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:34982025-09-29 10:23:52.896CONICET 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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1844614234872217600 |
score |
13.070432 |