Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid

Autores
Channar, Pervaiz Ali; Saeed, Aamer; Larik, Fayaz Ali; Batool, Bakhtawar; Kalsoom, Saima; Hasan, M.M.; Erben, Mauricio Federico; El-Seedi, Hesham R.; Ali, Musrat; Ashraf, Zaman
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Aryl pyrazoles are well recognized class of heterocyclic compounds found in several commercially available drugs. Owing to their significance in medicinal chemistry, in this current account we have synthesized a series of suitably substituted aryl pyrazole by employing Suzuki cross-coupling reaction. All compounds were evaluated for inhibition of mushroom tyrosinase enzyme both in vitro and in silico. Compound 3f (IC 50 = 1.568 ± 0.01 µM) showed relatively better potential compared to reference kojic acid (IC 50 = 16.051 ± 1.27 µM). A comparative docking studies showed that compound 3f have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (−6.90 kcal/mol) as compared to Kojic acid. The 4-methoxy group in compound 3f shows 100% interaction with Cu. Compound 3f displayed hydrogen binding interaction with His61 and His94 at distance of 1.71 and 1.74 Å which might be responsible for higher activity compared to Kojic acid.
Fil: Channar, Pervaiz Ali. Quaid-i-azam University; Pakistán
Fil: Saeed, Aamer. Quaid-i-azam University; Pakistán
Fil: Larik, Fayaz Ali. Quaid-i-azam University; Pakistán
Fil: Batool, Bakhtawar. Quaid-i-azam University; Pakistán
Fil: Kalsoom, Saima. International Islamic University Islamabad; Pakistán
Fil: Hasan, M.M.. Pakistan Institute Of Engineering And Applied Sciences; Pakistán
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: El-Seedi, Hesham R.. Uppsala Biomedicinska Centrum;
Fil: Ali, Musrat. Quaid-i-azam University; Pakistán
Fil: Ashraf, Zaman. Allama Iqbal Open University; Pakistán
Materia
ARYL PYRAZOLES
IN SILICO MOLECULAR DOCKING STUDIES
IN VITRO MUSHROOM TYROSINASE ASSAY
KOJIC ACID
SUZUKI CROSS COUPLING
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:11336/87819
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/87819
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acidChannar, Pervaiz AliSaeed, AamerLarik, Fayaz AliBatool, BakhtawarKalsoom, SaimaHasan, M.M.Erben, Mauricio FedericoEl-Seedi, Hesham R.Ali, MusratAshraf, ZamanARYL PYRAZOLESIN SILICO MOLECULAR DOCKING STUDIESIN VITRO MUSHROOM TYROSINASE ASSAYKOJIC ACIDSUZUKI CROSS COUPLINGhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Aryl pyrazoles are well recognized class of heterocyclic compounds found in several commercially available drugs. Owing to their significance in medicinal chemistry, in this current account we have synthesized a series of suitably substituted aryl pyrazole by employing Suzuki cross-coupling reaction. All compounds were evaluated for inhibition of mushroom tyrosinase enzyme both in vitro and in silico. Compound 3f (IC 50 = 1.568 ± 0.01 µM) showed relatively better potential compared to reference kojic acid (IC 50 = 16.051 ± 1.27 µM). A comparative docking studies showed that compound 3f have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (−6.90 kcal/mol) as compared to Kojic acid. The 4-methoxy group in compound 3f shows 100% interaction with Cu. Compound 3f displayed hydrogen binding interaction with His61 and His94 at distance of 1.71 and 1.74 Å which might be responsible for higher activity compared to Kojic acid.Fil: Channar, Pervaiz Ali. Quaid-i-azam University; PakistánFil: Saeed, Aamer. Quaid-i-azam University; PakistánFil: Larik, Fayaz Ali. Quaid-i-azam University; PakistánFil: Batool, Bakhtawar. Quaid-i-azam University; PakistánFil: Kalsoom, Saima. International Islamic University Islamabad; PakistánFil: Hasan, M.M.. Pakistan Institute Of Engineering And Applied Sciences; PakistánFil: 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: El-Seedi, Hesham R.. Uppsala Biomedicinska Centrum;Fil: Ali, Musrat. Quaid-i-azam University; PakistánFil: Ashraf, Zaman. Allama Iqbal Open University; PakistánAcademic Press Inc Elsevier Science2018-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/87819Channar, Pervaiz Ali; Saeed, Aamer; Larik, Fayaz Ali; Batool, Bakhtawar; Kalsoom, Saima; et al.; Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid; Academic Press Inc Elsevier Science; Bioorganic Chemistry; 79; 9-2018; 293-3000045-2068CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bioorg.2018.04.026info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0045206818301937?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 Técnicas2025-09-29T10:23:29Zoai:ri.conicet.gov.ar:11336/87819instacron: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 10:23:29.636CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
title Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
spellingShingle Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
Channar, Pervaiz Ali
ARYL PYRAZOLES
IN SILICO MOLECULAR DOCKING STUDIES
IN VITRO MUSHROOM TYROSINASE ASSAY
KOJIC ACID
SUZUKI CROSS COUPLING
title_short Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
title_full Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
title_fullStr Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
title_full_unstemmed Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
title_sort Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid
dc.creator.none.fl_str_mv Channar, Pervaiz Ali
Saeed, Aamer
Larik, Fayaz Ali
Batool, Bakhtawar
Kalsoom, Saima
Hasan, M.M.
Erben, Mauricio Federico
El-Seedi, Hesham R.
Ali, Musrat
Ashraf, Zaman
author Channar, Pervaiz Ali
author_facet Channar, Pervaiz Ali
Saeed, Aamer
Larik, Fayaz Ali
Batool, Bakhtawar
Kalsoom, Saima
Hasan, M.M.
Erben, Mauricio Federico
El-Seedi, Hesham R.
Ali, Musrat
Ashraf, Zaman
author_role author
author2 Saeed, Aamer
Larik, Fayaz Ali
Batool, Bakhtawar
Kalsoom, Saima
Hasan, M.M.
Erben, Mauricio Federico
El-Seedi, Hesham R.
Ali, Musrat
Ashraf, Zaman
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ARYL PYRAZOLES
IN SILICO MOLECULAR DOCKING STUDIES
IN VITRO MUSHROOM TYROSINASE ASSAY
KOJIC ACID
SUZUKI CROSS COUPLING
topic ARYL PYRAZOLES
IN SILICO MOLECULAR DOCKING STUDIES
IN VITRO MUSHROOM TYROSINASE ASSAY
KOJIC ACID
SUZUKI CROSS COUPLING
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Aryl pyrazoles are well recognized class of heterocyclic compounds found in several commercially available drugs. Owing to their significance in medicinal chemistry, in this current account we have synthesized a series of suitably substituted aryl pyrazole by employing Suzuki cross-coupling reaction. All compounds were evaluated for inhibition of mushroom tyrosinase enzyme both in vitro and in silico. Compound 3f (IC 50 = 1.568 ± 0.01 µM) showed relatively better potential compared to reference kojic acid (IC 50 = 16.051 ± 1.27 µM). A comparative docking studies showed that compound 3f have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (−6.90 kcal/mol) as compared to Kojic acid. The 4-methoxy group in compound 3f shows 100% interaction with Cu. Compound 3f displayed hydrogen binding interaction with His61 and His94 at distance of 1.71 and 1.74 Å which might be responsible for higher activity compared to Kojic acid.
Fil: Channar, Pervaiz Ali. Quaid-i-azam University; Pakistán
Fil: Saeed, Aamer. Quaid-i-azam University; Pakistán
Fil: Larik, Fayaz Ali. Quaid-i-azam University; Pakistán
Fil: Batool, Bakhtawar. Quaid-i-azam University; Pakistán
Fil: Kalsoom, Saima. International Islamic University Islamabad; Pakistán
Fil: Hasan, M.M.. Pakistan Institute Of Engineering And Applied Sciences; Pakistán
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: El-Seedi, Hesham R.. Uppsala Biomedicinska Centrum;
Fil: Ali, Musrat. Quaid-i-azam University; Pakistán
Fil: Ashraf, Zaman. Allama Iqbal Open University; Pakistán
description Aryl pyrazoles are well recognized class of heterocyclic compounds found in several commercially available drugs. Owing to their significance in medicinal chemistry, in this current account we have synthesized a series of suitably substituted aryl pyrazole by employing Suzuki cross-coupling reaction. All compounds were evaluated for inhibition of mushroom tyrosinase enzyme both in vitro and in silico. Compound 3f (IC 50 = 1.568 ± 0.01 µM) showed relatively better potential compared to reference kojic acid (IC 50 = 16.051 ± 1.27 µM). A comparative docking studies showed that compound 3f have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (−6.90 kcal/mol) as compared to Kojic acid. The 4-methoxy group in compound 3f shows 100% interaction with Cu. Compound 3f displayed hydrogen binding interaction with His61 and His94 at distance of 1.71 and 1.74 Å which might be responsible for higher activity compared to Kojic acid.
publishDate 2018
dc.date.none.fl_str_mv 2018-09
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/11336/87819
Channar, Pervaiz Ali; Saeed, Aamer; Larik, Fayaz Ali; Batool, Bakhtawar; Kalsoom, Saima; et al.; Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid; Academic Press Inc Elsevier Science; Bioorganic Chemistry; 79; 9-2018; 293-300
0045-2068
CONICET Digital
CONICET
url http://hdl.handle.net/11336/87819
identifier_str_mv Channar, Pervaiz Ali; Saeed, Aamer; Larik, Fayaz Ali; Batool, Bakhtawar; Kalsoom, Saima; et al.; Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid; Academic Press Inc Elsevier Science; Bioorganic Chemistry; 79; 9-2018; 293-300
0045-2068
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.bioorg.2018.04.026
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0045206818301937?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 Academic Press Inc Elsevier Science
publisher.none.fl_str_mv Academic Press Inc 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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score 13.070432

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