Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition...

Autores
Channar, Pervaiz Ali; Afzal, Saira; Ejaz, Syeda Abida; Saeed, Aamer; Larik, Fayaz Ali; Mahesar, Parvez Ali; Lecka, Joanna; Sévigny, Jean; Erben, Mauricio Federico; Iqbal, Jamshed
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the present work we report the synthesis of new aryl pyrazole derivatives using 1,3-dicarbonyl motifs. The reaction was proceeded by the cyclization of pentane-2,4-dione (1a), 3-chloropentane-2,4-dione (1b) or ethyl 3-oxobutanoate (1c) with different aryl hydrazines. The products, which can be regarded as 1H-pyrazol-1-yl-one analogues (3a-f, 3g-o, 4a-c, 5a-b) and represent drug like molecules along with well-developed structure?activity relationships, were obtained in good to excellent yield. The structures of synthesized compounds were charcterized on the basis of FT-IR, 1H NMR, 13C NMR and mass spectroscopic data. Considering alkaline phosphatases (APs), nucleotide pyrophosphatases/phosphodiesterases (NPPs) and nucleoside triphosphate diphosphohydrolase as the molecular targets, the effects of these synthesized compounds were investigated on different isozymes of APs, NPPs and NTPDases. The data revealed that the synthesized compounds inhibited both enzymes but most of them inhibited tissue non-specific alkaline phosphatase (TNAP) more selectively. The antitumor activity results indicated that the synthesized derivatives have strong inhibitory effects on the growth of selected cell lines from different tissues such as breast, bone marrow and cervix (MCF-7, K-562 and Hela) but with varying intensities. Moreover the binding mode of interactions were explained on the basis of molecular docking and in-silico studies.
Fil: Channar, Pervaiz Ali. Quaid-i-azam University; Pakistán
Fil: Afzal, Saira. Comsats University Islamabad; Pakistán
Fil: Ejaz, Syeda Abida. Comsats University Islamabad; Pakistán
Fil: Saeed, Aamer. Quaid-i-azam University; Pakistán
Fil: Larik, Fayaz Ali. Quaid-i-azam University; Pakistán
Fil: Mahesar, Parvez Ali. Quaid-i-azam University; Pakistán. Shah Abdul Latif University; Pakistán
Fil: Lecka, Joanna. Laval University; Canadá
Fil: Sévigny, Jean. Laval University; Canadá
Fil: Erben, Mauricio Federico. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Iqbal, Jamshed. Comsats University Islamabad; Pakistán
Materia
ALKALINE PHOSPHATASES (APS)
ANTITUMOR ACTIVITY
HYDRAZIDES
NUCLEOTIDE PYROPHOSPHATASES (NPPS)
PYRAZOLES
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:11336/87817
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/87817
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profileChannar, Pervaiz AliAfzal, SairaEjaz, Syeda AbidaSaeed, AamerLarik, Fayaz AliMahesar, Parvez AliLecka, JoannaSévigny, JeanErben, Mauricio FedericoIqbal, JamshedALKALINE PHOSPHATASES (APS)ANTITUMOR ACTIVITYHYDRAZIDESNUCLEOTIDE PYROPHOSPHATASES (NPPS)PYRAZOLEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In the present work we report the synthesis of new aryl pyrazole derivatives using 1,3-dicarbonyl motifs. The reaction was proceeded by the cyclization of pentane-2,4-dione (1a), 3-chloropentane-2,4-dione (1b) or ethyl 3-oxobutanoate (1c) with different aryl hydrazines. The products, which can be regarded as 1H-pyrazol-1-yl-one analogues (3a-f, 3g-o, 4a-c, 5a-b) and represent drug like molecules along with well-developed structure?activity relationships, were obtained in good to excellent yield. The structures of synthesized compounds were charcterized on the basis of FT-IR, 1H NMR, 13C NMR and mass spectroscopic data. Considering alkaline phosphatases (APs), nucleotide pyrophosphatases/phosphodiesterases (NPPs) and nucleoside triphosphate diphosphohydrolase as the molecular targets, the effects of these synthesized compounds were investigated on different isozymes of APs, NPPs and NTPDases. The data revealed that the synthesized compounds inhibited both enzymes but most of them inhibited tissue non-specific alkaline phosphatase (TNAP) more selectively. The antitumor activity results indicated that the synthesized derivatives have strong inhibitory effects on the growth of selected cell lines from different tissues such as breast, bone marrow and cervix (MCF-7, K-562 and Hela) but with varying intensities. Moreover the binding mode of interactions were explained on the basis of molecular docking and in-silico studies.Fil: Channar, Pervaiz Ali. Quaid-i-azam University; PakistánFil: Afzal, Saira. Comsats University Islamabad; PakistánFil: Ejaz, Syeda Abida. Comsats University Islamabad; PakistánFil: Saeed, Aamer. Quaid-i-azam University; PakistánFil: Larik, Fayaz Ali. Quaid-i-azam University; PakistánFil: Mahesar, Parvez Ali. Quaid-i-azam University; Pakistán. Shah Abdul Latif University; PakistánFil: Lecka, Joanna. Laval University; CanadáFil: Sévigny, Jean. Laval University; CanadáFil: Erben, Mauricio Federico. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Iqbal, Jamshed. Comsats University Islamabad; PakistánElsevier France-editions Scientifiques Medicales Elsevier2018-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/87817Channar, Pervaiz Ali; Afzal, Saira; Ejaz, Syeda Abida; Saeed, Aamer; Larik, Fayaz Ali; et al.; Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 156; 8-2018; 461-4780223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2018.07.002info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523418305580?via%3Dihubinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:49:02Zoai:ri.conicet.gov.ar:11336/87817instacron: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 09:49:02.513CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
title Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
spellingShingle Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
Channar, Pervaiz Ali
ALKALINE PHOSPHATASES (APS)
ANTITUMOR ACTIVITY
HYDRAZIDES
NUCLEOTIDE PYROPHOSPHATASES (NPPS)
PYRAZOLES
title_short Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
title_full Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
title_fullStr Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
title_full_unstemmed Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
title_sort Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile
dc.creator.none.fl_str_mv Channar, Pervaiz Ali
Afzal, Saira
Ejaz, Syeda Abida
Saeed, Aamer
Larik, Fayaz Ali
Mahesar, Parvez Ali
Lecka, Joanna
Sévigny, Jean
Erben, Mauricio Federico
Iqbal, Jamshed
author Channar, Pervaiz Ali
author_facet Channar, Pervaiz Ali
Afzal, Saira
Ejaz, Syeda Abida
Saeed, Aamer
Larik, Fayaz Ali
Mahesar, Parvez Ali
Lecka, Joanna
Sévigny, Jean
Erben, Mauricio Federico
Iqbal, Jamshed
author_role author
author2 Afzal, Saira
Ejaz, Syeda Abida
Saeed, Aamer
Larik, Fayaz Ali
Mahesar, Parvez Ali
Lecka, Joanna
Sévigny, Jean
Erben, Mauricio Federico
Iqbal, Jamshed
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ALKALINE PHOSPHATASES (APS)
ANTITUMOR ACTIVITY
HYDRAZIDES
NUCLEOTIDE PYROPHOSPHATASES (NPPS)
PYRAZOLES
topic ALKALINE PHOSPHATASES (APS)
ANTITUMOR ACTIVITY
HYDRAZIDES
NUCLEOTIDE PYROPHOSPHATASES (NPPS)
PYRAZOLES
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 the present work we report the synthesis of new aryl pyrazole derivatives using 1,3-dicarbonyl motifs. The reaction was proceeded by the cyclization of pentane-2,4-dione (1a), 3-chloropentane-2,4-dione (1b) or ethyl 3-oxobutanoate (1c) with different aryl hydrazines. The products, which can be regarded as 1H-pyrazol-1-yl-one analogues (3a-f, 3g-o, 4a-c, 5a-b) and represent drug like molecules along with well-developed structure?activity relationships, were obtained in good to excellent yield. The structures of synthesized compounds were charcterized on the basis of FT-IR, 1H NMR, 13C NMR and mass spectroscopic data. Considering alkaline phosphatases (APs), nucleotide pyrophosphatases/phosphodiesterases (NPPs) and nucleoside triphosphate diphosphohydrolase as the molecular targets, the effects of these synthesized compounds were investigated on different isozymes of APs, NPPs and NTPDases. The data revealed that the synthesized compounds inhibited both enzymes but most of them inhibited tissue non-specific alkaline phosphatase (TNAP) more selectively. The antitumor activity results indicated that the synthesized derivatives have strong inhibitory effects on the growth of selected cell lines from different tissues such as breast, bone marrow and cervix (MCF-7, K-562 and Hela) but with varying intensities. Moreover the binding mode of interactions were explained on the basis of molecular docking and in-silico studies.
Fil: Channar, Pervaiz Ali. Quaid-i-azam University; Pakistán
Fil: Afzal, Saira. Comsats University Islamabad; Pakistán
Fil: Ejaz, Syeda Abida. Comsats University Islamabad; Pakistán
Fil: Saeed, Aamer. Quaid-i-azam University; Pakistán
Fil: Larik, Fayaz Ali. Quaid-i-azam University; Pakistán
Fil: Mahesar, Parvez Ali. Quaid-i-azam University; Pakistán. Shah Abdul Latif University; Pakistán
Fil: Lecka, Joanna. Laval University; Canadá
Fil: Sévigny, Jean. Laval University; Canadá
Fil: Erben, Mauricio Federico. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Iqbal, Jamshed. Comsats University Islamabad; Pakistán
description In the present work we report the synthesis of new aryl pyrazole derivatives using 1,3-dicarbonyl motifs. The reaction was proceeded by the cyclization of pentane-2,4-dione (1a), 3-chloropentane-2,4-dione (1b) or ethyl 3-oxobutanoate (1c) with different aryl hydrazines. The products, which can be regarded as 1H-pyrazol-1-yl-one analogues (3a-f, 3g-o, 4a-c, 5a-b) and represent drug like molecules along with well-developed structure?activity relationships, were obtained in good to excellent yield. The structures of synthesized compounds were charcterized on the basis of FT-IR, 1H NMR, 13C NMR and mass spectroscopic data. Considering alkaline phosphatases (APs), nucleotide pyrophosphatases/phosphodiesterases (NPPs) and nucleoside triphosphate diphosphohydrolase as the molecular targets, the effects of these synthesized compounds were investigated on different isozymes of APs, NPPs and NTPDases. The data revealed that the synthesized compounds inhibited both enzymes but most of them inhibited tissue non-specific alkaline phosphatase (TNAP) more selectively. The antitumor activity results indicated that the synthesized derivatives have strong inhibitory effects on the growth of selected cell lines from different tissues such as breast, bone marrow and cervix (MCF-7, K-562 and Hela) but with varying intensities. Moreover the binding mode of interactions were explained on the basis of molecular docking and in-silico studies.
publishDate 2018
dc.date.none.fl_str_mv 2018-08
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/11336/87817
Channar, Pervaiz Ali; Afzal, Saira; Ejaz, Syeda Abida; Saeed, Aamer; Larik, Fayaz Ali; et al.; Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 156; 8-2018; 461-478
0223-5234
CONICET Digital
CONICET
url http://hdl.handle.net/11336/87817
identifier_str_mv Channar, Pervaiz Ali; Afzal, Saira; Ejaz, Syeda Abida; Saeed, Aamer; Larik, Fayaz Ali; et al.; Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 156; 8-2018; 461-478
0223-5234
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.ejmech.2018.07.002
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523418305580?via%3Dihub
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 Elsevier France-editions Scientifiques Medicales Elsevier
publisher.none.fl_str_mv Elsevier France-editions Scientifiques Medicales Elsevier
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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score 13.070432

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