Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylat...

Autores
Ahmed, Muhammad Naeem; Andleeb, Hina; Fahim, Asmaa M.; Madni, Murtaza; Khan, Sher Wali; Kaboudin, Babak; Ibrahim, Mahmoud A.A.; Sidhom, Peter A.; Gil, Diego Mauricio
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this manuscript, we synthesized a novel ethyl 2-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5) from the reaction acetophenone with 3-methoxybenzaldehyde in basic condition to afford the chalcone derivative (3) which has ability to cyclized with thiosemicarbazide to afford the corresponding dihydro-1H-pyrazole-1-carbothioamide (4). Compound 4 easily reacts with ethyl-3‑bromo-2-oxopropanoate to give the ethyl-2-(5-(3-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5). The structure of the synthesized compound was confirmed through spectral analysis (FT-IR, 1HNMR, 13CNMR). Moreover, the crystal structure of compound (5) has been solved using single-crystal X-ray diffraction measurements. These results indicate that 5 crystallizes in the monoclinic crystal system in the P21/n space group. The solid-state structure is mainly stabilized by a combination of intermolecular interactions such as weak hydrogen bonds, Csingle bondH···π, π···π stacking and O···C tetrel bonding interactions involving the O-atom of the ester group and the C-atom of the methoxy moiety. In order to confirm the presence of the mentioned intermolecular contacts, we have performed Hirshfeld surface analysis and their associated two-dimensional fingerprint plots. In addition, the strength and nature of the intermolecular interactions have been evaluated by using different computational tools including QTAIM and NCIplot index analysis. Molecular docking analysis was performed with both the enantiomers of pyrazolyl thiazole carboxylate and it was found that 1R bounds deeply into the pocket than 1S, furthermore 1R and indomethacin forms hydrogen bonds while 1S do not. The Molecular results are in good agreement with the experimental data.
Fil: Ahmed, Muhammad Naeem. University Of Azad Jammu And Kashmir; Pakistán. Institute of Advanced Studies in Basic Sciences; Irán
Fil: Andleeb, Hina. Northeastern University; Estados Unidos
Fil: Fahim, Asmaa M.. National Research Center; Egipto
Fil: Madni, Murtaza. Quaiad-i-azam University; Pakistán
Fil: Khan, Sher Wali. Shaheed Bb University; Pakistán
Fil: Kaboudin, Babak. Institute Of Advanced Studies In Basic Sciences; Irán
Fil: Ibrahim, Mahmoud A.A.. Minia University; Egipto
Fil: Sidhom, Peter A.. Tanta University; Egipto
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
Materia
THIAZOLE-4-CARBOXYLATE
HIRSHFELD SURFACES
DFT CALCULATIONS
INTERMOLECULAR INTERACTIONS
QTAIM
NCIPLOT INDEX ANALYSIS
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:11336/260621
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/260621
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical studyAhmed, Muhammad NaeemAndleeb, HinaFahim, Asmaa M.Madni, MurtazaKhan, Sher WaliKaboudin, BabakIbrahim, Mahmoud A.A.Sidhom, Peter A.Gil, Diego MauricioTHIAZOLE-4-CARBOXYLATEHIRSHFELD SURFACESDFT CALCULATIONSINTERMOLECULAR INTERACTIONSQTAIMNCIPLOT INDEX ANALYSIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this manuscript, we synthesized a novel ethyl 2-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5) from the reaction acetophenone with 3-methoxybenzaldehyde in basic condition to afford the chalcone derivative (3) which has ability to cyclized with thiosemicarbazide to afford the corresponding dihydro-1H-pyrazole-1-carbothioamide (4). Compound 4 easily reacts with ethyl-3‑bromo-2-oxopropanoate to give the ethyl-2-(5-(3-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5). The structure of the synthesized compound was confirmed through spectral analysis (FT-IR, 1HNMR, 13CNMR). Moreover, the crystal structure of compound (5) has been solved using single-crystal X-ray diffraction measurements. These results indicate that 5 crystallizes in the monoclinic crystal system in the P21/n space group. The solid-state structure is mainly stabilized by a combination of intermolecular interactions such as weak hydrogen bonds, Csingle bondH···π, π···π stacking and O···C tetrel bonding interactions involving the O-atom of the ester group and the C-atom of the methoxy moiety. In order to confirm the presence of the mentioned intermolecular contacts, we have performed Hirshfeld surface analysis and their associated two-dimensional fingerprint plots. In addition, the strength and nature of the intermolecular interactions have been evaluated by using different computational tools including QTAIM and NCIplot index analysis. Molecular docking analysis was performed with both the enantiomers of pyrazolyl thiazole carboxylate and it was found that 1R bounds deeply into the pocket than 1S, furthermore 1R and indomethacin forms hydrogen bonds while 1S do not. The Molecular results are in good agreement with the experimental data.Fil: Ahmed, Muhammad Naeem. University Of Azad Jammu And Kashmir; Pakistán. Institute of Advanced Studies in Basic Sciences; IránFil: Andleeb, Hina. Northeastern University; Estados UnidosFil: Fahim, Asmaa M.. National Research Center; EgiptoFil: Madni, Murtaza. Quaiad-i-azam University; PakistánFil: Khan, Sher Wali. Shaheed Bb University; PakistánFil: Kaboudin, Babak. Institute Of Advanced Studies In Basic Sciences; IránFil: Ibrahim, Mahmoud A.A.. Minia University; EgiptoFil: Sidhom, Peter A.. Tanta University; EgiptoFil: 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; ArgentinaElsevier Science2024-01info: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/11336/260621Ahmed, Muhammad Naeem; Andleeb, Hina; Fahim, Asmaa M.; Madni, Murtaza; Khan, Sher Wali; et al.; Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study; Elsevier Science; Journal of Molecular Structure; 1296; 136908; 1-2024; 1-130022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2023.136908info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286023019981info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:02:17Zoai:ri.conicet.gov.ar:11336/260621instacron: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 11:02:17.443CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
title Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
spellingShingle Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
Ahmed, Muhammad Naeem
THIAZOLE-4-CARBOXYLATE
HIRSHFELD SURFACES
DFT CALCULATIONS
INTERMOLECULAR INTERACTIONS
QTAIM
NCIPLOT INDEX ANALYSIS
title_short Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
title_full Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
title_fullStr Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
title_full_unstemmed Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
title_sort Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study
dc.creator.none.fl_str_mv Ahmed, Muhammad Naeem
Andleeb, Hina
Fahim, Asmaa M.
Madni, Murtaza
Khan, Sher Wali
Kaboudin, Babak
Ibrahim, Mahmoud A.A.
Sidhom, Peter A.
Gil, Diego Mauricio
author Ahmed, Muhammad Naeem
author_facet Ahmed, Muhammad Naeem
Andleeb, Hina
Fahim, Asmaa M.
Madni, Murtaza
Khan, Sher Wali
Kaboudin, Babak
Ibrahim, Mahmoud A.A.
Sidhom, Peter A.
Gil, Diego Mauricio
author_role author
author2 Andleeb, Hina
Fahim, Asmaa M.
Madni, Murtaza
Khan, Sher Wali
Kaboudin, Babak
Ibrahim, Mahmoud A.A.
Sidhom, Peter A.
Gil, Diego Mauricio
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv THIAZOLE-4-CARBOXYLATE
HIRSHFELD SURFACES
DFT CALCULATIONS
INTERMOLECULAR INTERACTIONS
QTAIM
NCIPLOT INDEX ANALYSIS
topic THIAZOLE-4-CARBOXYLATE
HIRSHFELD SURFACES
DFT CALCULATIONS
INTERMOLECULAR INTERACTIONS
QTAIM
NCIPLOT INDEX ANALYSIS
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 manuscript, we synthesized a novel ethyl 2-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5) from the reaction acetophenone with 3-methoxybenzaldehyde in basic condition to afford the chalcone derivative (3) which has ability to cyclized with thiosemicarbazide to afford the corresponding dihydro-1H-pyrazole-1-carbothioamide (4). Compound 4 easily reacts with ethyl-3‑bromo-2-oxopropanoate to give the ethyl-2-(5-(3-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5). The structure of the synthesized compound was confirmed through spectral analysis (FT-IR, 1HNMR, 13CNMR). Moreover, the crystal structure of compound (5) has been solved using single-crystal X-ray diffraction measurements. These results indicate that 5 crystallizes in the monoclinic crystal system in the P21/n space group. The solid-state structure is mainly stabilized by a combination of intermolecular interactions such as weak hydrogen bonds, Csingle bondH···π, π···π stacking and O···C tetrel bonding interactions involving the O-atom of the ester group and the C-atom of the methoxy moiety. In order to confirm the presence of the mentioned intermolecular contacts, we have performed Hirshfeld surface analysis and their associated two-dimensional fingerprint plots. In addition, the strength and nature of the intermolecular interactions have been evaluated by using different computational tools including QTAIM and NCIplot index analysis. Molecular docking analysis was performed with both the enantiomers of pyrazolyl thiazole carboxylate and it was found that 1R bounds deeply into the pocket than 1S, furthermore 1R and indomethacin forms hydrogen bonds while 1S do not. The Molecular results are in good agreement with the experimental data.
Fil: Ahmed, Muhammad Naeem. University Of Azad Jammu And Kashmir; Pakistán. Institute of Advanced Studies in Basic Sciences; Irán
Fil: Andleeb, Hina. Northeastern University; Estados Unidos
Fil: Fahim, Asmaa M.. National Research Center; Egipto
Fil: Madni, Murtaza. Quaiad-i-azam University; Pakistán
Fil: Khan, Sher Wali. Shaheed Bb University; Pakistán
Fil: Kaboudin, Babak. Institute Of Advanced Studies In Basic Sciences; Irán
Fil: Ibrahim, Mahmoud A.A.. Minia University; Egipto
Fil: Sidhom, Peter A.. Tanta University; Egipto
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
description In this manuscript, we synthesized a novel ethyl 2-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5) from the reaction acetophenone with 3-methoxybenzaldehyde in basic condition to afford the chalcone derivative (3) which has ability to cyclized with thiosemicarbazide to afford the corresponding dihydro-1H-pyrazole-1-carbothioamide (4). Compound 4 easily reacts with ethyl-3‑bromo-2-oxopropanoate to give the ethyl-2-(5-(3-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole-4-carboxylate (5). The structure of the synthesized compound was confirmed through spectral analysis (FT-IR, 1HNMR, 13CNMR). Moreover, the crystal structure of compound (5) has been solved using single-crystal X-ray diffraction measurements. These results indicate that 5 crystallizes in the monoclinic crystal system in the P21/n space group. The solid-state structure is mainly stabilized by a combination of intermolecular interactions such as weak hydrogen bonds, Csingle bondH···π, π···π stacking and O···C tetrel bonding interactions involving the O-atom of the ester group and the C-atom of the methoxy moiety. In order to confirm the presence of the mentioned intermolecular contacts, we have performed Hirshfeld surface analysis and their associated two-dimensional fingerprint plots. In addition, the strength and nature of the intermolecular interactions have been evaluated by using different computational tools including QTAIM and NCIplot index analysis. Molecular docking analysis was performed with both the enantiomers of pyrazolyl thiazole carboxylate and it was found that 1R bounds deeply into the pocket than 1S, furthermore 1R and indomethacin forms hydrogen bonds while 1S do not. The Molecular results are in good agreement with the experimental data.
publishDate 2024
dc.date.none.fl_str_mv 2024-01
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/11336/260621
Ahmed, Muhammad Naeem; Andleeb, Hina; Fahim, Asmaa M.; Madni, Murtaza; Khan, Sher Wali; et al.; Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study; Elsevier Science; Journal of Molecular Structure; 1296; 136908; 1-2024; 1-13
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/260621
identifier_str_mv Ahmed, Muhammad Naeem; Andleeb, Hina; Fahim, Asmaa M.; Madni, Murtaza; Khan, Sher Wali; et al.; Supramolecular assembly involving weak hydrogen bonds, anti-parallel π···π stacking and O···C tetrel bonding interactions and LOX studies in a 1H-pyrazol-1-yl)thiazole-4-carboxylate derivative: An experimental and theoretical study; Elsevier Science; Journal of Molecular Structure; 1296; 136908; 1-2024; 1-13
0022-2860
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2023.136908
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286023019981
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 Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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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