Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases

Autores
Urbina, Juan M.; Cortés, Juan C. G.; Palma, Alirio; López, Silvia Noelí; Zacchino, Susana Alicia Stella; Enriz, Ricardo Daniel; Ribas, Juan C.; Kouznetzov, Vladimir V.
Año de publicación
2000
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
As part of our project devoted to the search for antifungal agents, which act via a selective mode of action, we synthesized a series of new 4- aryl- or 4-alkyl-N-arylamine-1-butenes and transformed some of them into 2- substituted 4-methyl-tetrahydroquinolines and quinolines by using a novel three-step synthesis. Results obtained in agar dilution assays have shown that 4-aryl homoallylamines not possessing halogen in their structures, tetrahydroquinolines and quinolines, display a range of antifungal properties in particular against Epidermophyton floccosum and Microsporum canis. Regarding the mode of action, all active compounds showed in vitro inhibitory activities against β(1-3) glucan-synthase and mainly against chitin- synthase. These enzymes catalyze the synthesis of β(1-3) glucan and chitin, respectively, major polymers of the fungal cell wall. Since fungal but not mammalian cells are encased in a cell wall, its inhibition may represent a useful mode of action for these antifungal compounds.
Fil: Urbina, Juan M.. Universidad Industrial Santander; Colombia
Fil: Cortés, Juan C. G.. Instituto de Microbiologı́a Bioquı́mica. Salamanca; España
Fil: Palma, Alirio. Universidad Industrial Santander; Colombia
Fil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Ribas, Juan C.. Instituto de Microbiologı́a Bioquı́mica. Salamanca; España
Fil: Kouznetzov, Vladimir V.. Universidad Industrial Santander; Colombia
Materia
Antifungal compounds
Quitin synthase inhibitors
Arylamines
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:11336/127110
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/127110
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthasesUrbina, Juan M.Cortés, Juan C. G.Palma, AlirioLópez, Silvia NoelíZacchino, Susana Alicia StellaEnriz, Ricardo DanielRibas, Juan C.Kouznetzov, Vladimir V.Antifungal compoundsQuitin synthase inhibitorsArylamineshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1As part of our project devoted to the search for antifungal agents, which act via a selective mode of action, we synthesized a series of new 4- aryl- or 4-alkyl-N-arylamine-1-butenes and transformed some of them into 2- substituted 4-methyl-tetrahydroquinolines and quinolines by using a novel three-step synthesis. Results obtained in agar dilution assays have shown that 4-aryl homoallylamines not possessing halogen in their structures, tetrahydroquinolines and quinolines, display a range of antifungal properties in particular against Epidermophyton floccosum and Microsporum canis. Regarding the mode of action, all active compounds showed in vitro inhibitory activities against β(1-3) glucan-synthase and mainly against chitin- synthase. These enzymes catalyze the synthesis of β(1-3) glucan and chitin, respectively, major polymers of the fungal cell wall. Since fungal but not mammalian cells are encased in a cell wall, its inhibition may represent a useful mode of action for these antifungal compounds.Fil: Urbina, Juan M.. Universidad Industrial Santander; ColombiaFil: Cortés, Juan C. G.. Instituto de Microbiologı́a Bioquı́mica. Salamanca; EspañaFil: Palma, Alirio. Universidad Industrial Santander; ColombiaFil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Ribas, Juan C.. Instituto de Microbiologı́a Bioquı́mica. Salamanca; EspañaFil: Kouznetzov, Vladimir V.. Universidad Industrial Santander; ColombiaPergamon-Elsevier Science Ltd2000-04info: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/11336/127110Urbina, Juan M.; Cortés, Juan C. G.; Palma, Alirio; López, Silvia Noelí; Zacchino, Susana Alicia Stella; et al.; Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 8; 4; 4-2000; 691-6980968-0896CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0968089600000031info:eu-repo/semantics/altIdentifier/doi/10.1016/s0968-0896(00)00003-1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:03:38Zoai:ri.conicet.gov.ar:11336/127110instacron: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 10:03:39.022CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
title Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
spellingShingle Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
Urbina, Juan M.
Antifungal compounds
Quitin synthase inhibitors
Arylamines
title_short Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
title_full Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
title_fullStr Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
title_full_unstemmed Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
title_sort Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases
dc.creator.none.fl_str_mv Urbina, Juan M.
Cortés, Juan C. G.
Palma, Alirio
López, Silvia Noelí
Zacchino, Susana Alicia Stella
Enriz, Ricardo Daniel
Ribas, Juan C.
Kouznetzov, Vladimir V.
author Urbina, Juan M.
author_facet Urbina, Juan M.
Cortés, Juan C. G.
Palma, Alirio
López, Silvia Noelí
Zacchino, Susana Alicia Stella
Enriz, Ricardo Daniel
Ribas, Juan C.
Kouznetzov, Vladimir V.
author_role author
author2 Cortés, Juan C. G.
Palma, Alirio
López, Silvia Noelí
Zacchino, Susana Alicia Stella
Enriz, Ricardo Daniel
Ribas, Juan C.
Kouznetzov, Vladimir V.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Antifungal compounds
Quitin synthase inhibitors
Arylamines
topic Antifungal compounds
Quitin synthase inhibitors
Arylamines
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv As part of our project devoted to the search for antifungal agents, which act via a selective mode of action, we synthesized a series of new 4- aryl- or 4-alkyl-N-arylamine-1-butenes and transformed some of them into 2- substituted 4-methyl-tetrahydroquinolines and quinolines by using a novel three-step synthesis. Results obtained in agar dilution assays have shown that 4-aryl homoallylamines not possessing halogen in their structures, tetrahydroquinolines and quinolines, display a range of antifungal properties in particular against Epidermophyton floccosum and Microsporum canis. Regarding the mode of action, all active compounds showed in vitro inhibitory activities against β(1-3) glucan-synthase and mainly against chitin- synthase. These enzymes catalyze the synthesis of β(1-3) glucan and chitin, respectively, major polymers of the fungal cell wall. Since fungal but not mammalian cells are encased in a cell wall, its inhibition may represent a useful mode of action for these antifungal compounds.
Fil: Urbina, Juan M.. Universidad Industrial Santander; Colombia
Fil: Cortés, Juan C. G.. Instituto de Microbiologı́a Bioquı́mica. Salamanca; España
Fil: Palma, Alirio. Universidad Industrial Santander; Colombia
Fil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Ribas, Juan C.. Instituto de Microbiologı́a Bioquı́mica. Salamanca; España
Fil: Kouznetzov, Vladimir V.. Universidad Industrial Santander; Colombia
description As part of our project devoted to the search for antifungal agents, which act via a selective mode of action, we synthesized a series of new 4- aryl- or 4-alkyl-N-arylamine-1-butenes and transformed some of them into 2- substituted 4-methyl-tetrahydroquinolines and quinolines by using a novel three-step synthesis. Results obtained in agar dilution assays have shown that 4-aryl homoallylamines not possessing halogen in their structures, tetrahydroquinolines and quinolines, display a range of antifungal properties in particular against Epidermophyton floccosum and Microsporum canis. Regarding the mode of action, all active compounds showed in vitro inhibitory activities against β(1-3) glucan-synthase and mainly against chitin- synthase. These enzymes catalyze the synthesis of β(1-3) glucan and chitin, respectively, major polymers of the fungal cell wall. Since fungal but not mammalian cells are encased in a cell wall, its inhibition may represent a useful mode of action for these antifungal compounds.
publishDate 2000
dc.date.none.fl_str_mv 2000-04
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/11336/127110
Urbina, Juan M.; Cortés, Juan C. G.; Palma, Alirio; López, Silvia Noelí; Zacchino, Susana Alicia Stella; et al.; Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 8; 4; 4-2000; 691-698
0968-0896
CONICET Digital
CONICET
url http://hdl.handle.net/11336/127110
identifier_str_mv Urbina, Juan M.; Cortés, Juan C. G.; Palma, Alirio; López, Silvia Noelí; Zacchino, Susana Alicia Stella; et al.; Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1- butenes and related compounds with inhibitory activities on β(1-3) glucan and chitin synthases; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 8; 4; 4-2000; 691-698
0968-0896
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0968089600000031
info:eu-repo/semantics/altIdentifier/doi/10.1016/s0968-0896(00)00003-1
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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score 13.070432

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