One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity

A series of 5-methyl-3,4-diaryl-substituted 1H-pyrazoles, N-isosteres of valdecoxib, was synthesized by a [3+2] cycloaddition/[1,5] sigmatropic rearrangement sequence starting from tosylhydrazine, aryl methyl ketones and terminal aryl alkynes bearing various substituents (H, Me, OMe, F, SO2Me, SO2NH...

Descripción completa

Detalles Bibliográficos
Autores: Roscales García, Silvia, Bechmann, Nicole, Pietzsch, Jens, Kniess, Torsten
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/126401
Acceso en línea:https://hdl.handle.net/20.500.14352/126401
Access Level:acceso abierto
Palabra clave:547
Química orgánica (Química)
2306 Química Orgánica
id ES_db7536ec79772a4d3e36720f5f73b598
oai_identifier_str oai:docta.ucm.es:20.500.14352/126401
network_acronym_str ES
network_name_str España
repository_id_str
spelling One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activityRoscales García, SilviaBechmann, NicolePietzsch, JensKniess, Torsten547Química orgánica (Química)2306 Química OrgánicaA series of 5-methyl-3,4-diaryl-substituted 1H-pyrazoles, N-isosteres of valdecoxib, was synthesized by a [3+2] cycloaddition/[1,5] sigmatropic rearrangement sequence starting from tosylhydrazine, aryl methyl ketones and terminal aryl alkynes bearing various substituents (H, Me, OMe, F, SO2Me, SO2NH2). New pyrazoles were prepared regioselectively in a one-pot process with moderate-good yields. All compounds were used in in vitro cyclooxygenase (COX) assays to determine inhibitory potency and selectivity to COX-1 and COX-2. In general, these new pyrazoles are characterized by selective COX-2 inhibition activity in a micromolar range.Universidad Complutense de Madrid20192019-01-0120192019-01-01journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/126401reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1264012026-06-02T12:44:21Z
dc.title.none.fl_str_mv One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
title One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
spellingShingle One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
Roscales García, Silvia
547
Química orgánica (Química)
2306 Química Orgánica
title_short One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
title_full One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
title_fullStr One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
title_full_unstemmed One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
title_sort One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
dc.creator.none.fl_str_mv Roscales García, Silvia
Bechmann, Nicole
Pietzsch, Jens
Kniess, Torsten
author Roscales García, Silvia
author_facet Roscales García, Silvia
Bechmann, Nicole
Pietzsch, Jens
Kniess, Torsten
author_role author
author2 Bechmann, Nicole
Pietzsch, Jens
Kniess, Torsten
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Química orgánica (Química)
2306 Química Orgánica
topic 547
Química orgánica (Química)
2306 Química Orgánica
description A series of 5-methyl-3,4-diaryl-substituted 1H-pyrazoles, N-isosteres of valdecoxib, was synthesized by a [3+2] cycloaddition/[1,5] sigmatropic rearrangement sequence starting from tosylhydrazine, aryl methyl ketones and terminal aryl alkynes bearing various substituents (H, Me, OMe, F, SO2Me, SO2NH2). New pyrazoles were prepared regioselectively in a one-pot process with moderate-good yields. All compounds were used in in vitro cyclooxygenase (COX) assays to determine inhibitory potency and selectivity to COX-1 and COX-2. In general, these new pyrazoles are characterized by selective COX-2 inhibition activity in a micromolar range.
publishDate 2019
dc.date.none.fl_str_mv 2019
2019-01-01
2019
2019-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/126401
url https://hdl.handle.net/20.500.14352/126401
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869421677264240640
score 15,811543

Similares en LA Referencia