Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase

Autores
Muscia, Gisela Celeste; Hautmann, Stephanie; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Gütschow, Michael
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a–l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol-3-yl)-6-nitro-4-phenylquinoline (10l; IC50 = 1.98 μM) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode.
Fil: Muscia, Gisela Celeste. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Hautmann, Stephanie. Universitaet Bonn; Alemania
Fil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Asís, Silvia Elizabeth. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Gütschow, Michael. Universitaet Bonn; Alemania
Materia
Cholesterol Esterase
Quinolines
Friedländer Reaction
Mixed-Type Inhibition
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/16525
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/16525
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esteraseMuscia, Gisela CelesteHautmann, StephanieBuldain, Graciela YolandaAsís, Silvia ElizabethGütschow, MichaelCholesterol EsteraseQuinolinesFriedländer ReactionMixed-Type Inhibitionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a–l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol-3-yl)-6-nitro-4-phenylquinoline (10l; IC50 = 1.98 μM) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode.Fil: Muscia, Gisela Celeste. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Hautmann, Stephanie. Universitaet Bonn; AlemaniaFil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Asís, Silvia Elizabeth. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Gütschow, Michael. Universitaet Bonn; AlemaniaElsevier2014-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/16525Muscia, Gisela Celeste; Hautmann, Stephanie; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Gütschow, Michael; Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase; Elsevier; Bioorganic & Medicinal Chemistry Letters; 24; 6; 3-2014; 1545-15490960-894Xenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X14001218info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2014.01.081info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:16:13Zoai:ri.conicet.gov.ar:11336/16525instacron: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 10:16:13.734CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
title Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
spellingShingle Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
Muscia, Gisela Celeste
Cholesterol Esterase
Quinolines
Friedländer Reaction
Mixed-Type Inhibition
title_short Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
title_full Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
title_fullStr Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
title_full_unstemmed Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
title_sort Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
dc.creator.none.fl_str_mv Muscia, Gisela Celeste
Hautmann, Stephanie
Buldain, Graciela Yolanda
Asís, Silvia Elizabeth
Gütschow, Michael
author Muscia, Gisela Celeste
author_facet Muscia, Gisela Celeste
Hautmann, Stephanie
Buldain, Graciela Yolanda
Asís, Silvia Elizabeth
Gütschow, Michael
author_role author
author2 Hautmann, Stephanie
Buldain, Graciela Yolanda
Asís, Silvia Elizabeth
Gütschow, Michael
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cholesterol Esterase
Quinolines
Friedländer Reaction
Mixed-Type Inhibition
topic Cholesterol Esterase
Quinolines
Friedländer Reaction
Mixed-Type Inhibition
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 series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a–l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol-3-yl)-6-nitro-4-phenylquinoline (10l; IC50 = 1.98 μM) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode.
Fil: Muscia, Gisela Celeste. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Hautmann, Stephanie. Universitaet Bonn; Alemania
Fil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Asís, Silvia Elizabeth. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Gütschow, Michael. Universitaet Bonn; Alemania
description A series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a–l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol-3-yl)-6-nitro-4-phenylquinoline (10l; IC50 = 1.98 μM) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode.
publishDate 2014
dc.date.none.fl_str_mv 2014-03
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/11336/16525
Muscia, Gisela Celeste; Hautmann, Stephanie; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Gütschow, Michael; Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase; Elsevier; Bioorganic & Medicinal Chemistry Letters; 24; 6; 3-2014; 1545-1549
0960-894X
url http://hdl.handle.net/11336/16525
identifier_str_mv Muscia, Gisela Celeste; Hautmann, Stephanie; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Gütschow, Michael; Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase; Elsevier; Bioorganic & Medicinal Chemistry Letters; 24; 6; 3-2014; 1545-1549
0960-894X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X14001218
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2014.01.081
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv 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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