Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety
- Autores
- Riafrecha, Leonardo Ezequiel; Bua, Silvia; Supuran, Claudiu T.; Colinas, Pedro Alfonso
- Año de publicación
- 2016
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- A small series of N-glycosylsulfonamides incorporating the phenol moiety has been prepared by Ferrier sulfonamidoglycosylation of D-glycals. N-Glycosides were tested for the inhibition of four isoforms of carbonic anhydrase. In this study, all compounds showed good inhibitory activity against hCA I and II, with selectivity against the cytosolic hCA II versus the tumor associated isozymes. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves and enhances its inhibitory activity.
Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Bua, Silvia. Università degli Studi di Firenze; Italia
Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia
Fil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina - Materia
-
Carbonic Anhyrases
Glycomimetic
Sulfonamidoglycosylation - 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:11336/54631
Ver los metadatos del registro completo
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Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moietyRiafrecha, Leonardo EzequielBua, SilviaSupuran, Claudiu T.Colinas, Pedro AlfonsoCarbonic AnhyrasesGlycomimeticSulfonamidoglycosylationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A small series of N-glycosylsulfonamides incorporating the phenol moiety has been prepared by Ferrier sulfonamidoglycosylation of D-glycals. N-Glycosides were tested for the inhibition of four isoforms of carbonic anhydrase. In this study, all compounds showed good inhibitory activity against hCA I and II, with selectivity against the cytosolic hCA II versus the tumor associated isozymes. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves and enhances its inhibitory activity.Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Bua, Silvia. Università degli Studi di Firenze; ItaliaFil: Supuran, Claudiu T.. Università degli Studi di Firenze; ItaliaFil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaPergamon-Elsevier Science Ltd2016-07info: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/11336/54631Riafrecha, Leonardo Ezequiel; Bua, Silvia; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 26; 16; 7-2016; 3892-38950960-894XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2016.07.015info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X1630717Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:32:20Zoai:ri.conicet.gov.ar:11336/54631instacron: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 09:32:20.532CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
title |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
spellingShingle |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety Riafrecha, Leonardo Ezequiel Carbonic Anhyrases Glycomimetic Sulfonamidoglycosylation |
title_short |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
title_full |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
title_fullStr |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
title_full_unstemmed |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
title_sort |
Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety |
dc.creator.none.fl_str_mv |
Riafrecha, Leonardo Ezequiel Bua, Silvia Supuran, Claudiu T. Colinas, Pedro Alfonso |
author |
Riafrecha, Leonardo Ezequiel |
author_facet |
Riafrecha, Leonardo Ezequiel Bua, Silvia Supuran, Claudiu T. Colinas, Pedro Alfonso |
author_role |
author |
author2 |
Bua, Silvia Supuran, Claudiu T. Colinas, Pedro Alfonso |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
Carbonic Anhyrases Glycomimetic Sulfonamidoglycosylation |
topic |
Carbonic Anhyrases Glycomimetic Sulfonamidoglycosylation |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
A small series of N-glycosylsulfonamides incorporating the phenol moiety has been prepared by Ferrier sulfonamidoglycosylation of D-glycals. N-Glycosides were tested for the inhibition of four isoforms of carbonic anhydrase. In this study, all compounds showed good inhibitory activity against hCA I and II, with selectivity against the cytosolic hCA II versus the tumor associated isozymes. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves and enhances its inhibitory activity. Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina Fil: Bua, Silvia. Università degli Studi di Firenze; Italia Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia Fil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina |
description |
A small series of N-glycosylsulfonamides incorporating the phenol moiety has been prepared by Ferrier sulfonamidoglycosylation of D-glycals. N-Glycosides were tested for the inhibition of four isoforms of carbonic anhydrase. In this study, all compounds showed good inhibitory activity against hCA I and II, with selectivity against the cytosolic hCA II versus the tumor associated isozymes. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves and enhances its inhibitory activity. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-07 |
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/11336/54631 Riafrecha, Leonardo Ezequiel; Bua, Silvia; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 26; 16; 7-2016; 3892-3895 0960-894X CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/54631 |
identifier_str_mv |
Riafrecha, Leonardo Ezequiel; Bua, Silvia; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 26; 16; 7-2016; 3892-3895 0960-894X 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.bmcl.2016.07.015 info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X1630717X |
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 |
Pergamon-Elsevier Science Ltd |
publisher.none.fl_str_mv |
Pergamon-Elsevier Science Ltd |
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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1844612985607159808 |
score |
13.070432 |