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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/260621
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oai:ri.conicet.gov.ar:11336/260621 |
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3498 |
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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 Técnicas2025-09-29T09:34:14Zoai: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:34982025-09-29 09:34:15.2CONICET 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 |
_version_ |
1844613058633138176 |
score |
13.070432 |