Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH

Autores
Larghi, Enrique Leandro; Operto, María Alejandra; Torres, Nelson René; Kaufman, Teodoro Saul
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of carboxylic acids carrying various functionalization on C-7 of their common 3H-spiro[benzofuran-2,1?-cyclohexane] skeleton were synthesized from filifolinol, as analogs of the natural Complement inhibitor K76-COOH. In order to probe the relevance of the C-7 functionalization on their bioactivity, the ability of the analogs to inhibit Complement activation through the classical pathway was determined. The observed results suggest that functionalization of C-7 can modulate the inhibitory activity of the tested compounds. The 7-trifluoromethyl derivative was the compound with the lowest IC50 value among the tested analogs, being more potent than K76-COOH.
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Operto, María Alejandra. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Torres, Nelson René. Universidad de Santiago de Chile; Chile
Fil: Kaufman, Teodoro Saul. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
Filifolinol derivatives
C-7 functionalization
Complement inhibitors
Classical pathway
K76-COOH analogs
Pd-Catalyzed C-C bond formation
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:11336/105021
Acceder
id CONICETDig_1a49cc07348b4328da6f2c20896a57cd
oai_identifier_str oai:ri.conicet.gov.ar:11336/105021
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOHLarghi, Enrique LeandroOperto, María AlejandraTorres, Nelson RenéKaufman, Teodoro SaulFilifolinol derivativesC-7 functionalizationComplement inhibitorsClassical pathwayK76-COOH analogsPd-Catalyzed C-C bond formationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of carboxylic acids carrying various functionalization on C-7 of their common 3H-spiro[benzofuran-2,1?-cyclohexane] skeleton were synthesized from filifolinol, as analogs of the natural Complement inhibitor K76-COOH. In order to probe the relevance of the C-7 functionalization on their bioactivity, the ability of the analogs to inhibit Complement activation through the classical pathway was determined. The observed results suggest that functionalization of C-7 can modulate the inhibitory activity of the tested compounds. The 7-trifluoromethyl derivative was the compound with the lowest IC50 value among the tested analogs, being more potent than K76-COOH.Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; ArgentinaFil: Operto, María Alejandra. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; ArgentinaFil: Torres, Nelson René. Universidad de Santiago de Chile; ChileFil: Kaufman, Teodoro Saul. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaElsevier France-editions Scientifiques Medicales Elsevier2012-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/105021Larghi, Enrique Leandro; Operto, María Alejandra; Torres, Nelson René; Kaufman, Teodoro Saul; Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 55; 9-2012; 74-840223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2012.07.003info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0223523412004151info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:34:11Zoai:ri.conicet.gov.ar:11336/105021instacron: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 09:34:11.749CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
title Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
spellingShingle Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
Larghi, Enrique Leandro
Filifolinol derivatives
C-7 functionalization
Complement inhibitors
Classical pathway
K76-COOH analogs
Pd-Catalyzed C-C bond formation
title_short Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
title_full Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
title_fullStr Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
title_full_unstemmed Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
title_sort Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH
dc.creator.none.fl_str_mv Larghi, Enrique Leandro
Operto, María Alejandra
Torres, Nelson René
Kaufman, Teodoro Saul
author Larghi, Enrique Leandro
author_facet Larghi, Enrique Leandro
Operto, María Alejandra
Torres, Nelson René
Kaufman, Teodoro Saul
author_role author
author2 Operto, María Alejandra
Torres, Nelson René
Kaufman, Teodoro Saul
author2_role author
author
author
dc.subject.none.fl_str_mv Filifolinol derivatives
C-7 functionalization
Complement inhibitors
Classical pathway
K76-COOH analogs
Pd-Catalyzed C-C bond formation
topic Filifolinol derivatives
C-7 functionalization
Complement inhibitors
Classical pathway
K76-COOH analogs
Pd-Catalyzed C-C bond formation
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 carboxylic acids carrying various functionalization on C-7 of their common 3H-spiro[benzofuran-2,1?-cyclohexane] skeleton were synthesized from filifolinol, as analogs of the natural Complement inhibitor K76-COOH. In order to probe the relevance of the C-7 functionalization on their bioactivity, the ability of the analogs to inhibit Complement activation through the classical pathway was determined. The observed results suggest that functionalization of C-7 can modulate the inhibitory activity of the tested compounds. The 7-trifluoromethyl derivative was the compound with the lowest IC50 value among the tested analogs, being more potent than K76-COOH.
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Operto, María Alejandra. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Torres, Nelson René. Universidad de Santiago de Chile; Chile
Fil: Kaufman, Teodoro Saul. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description A series of carboxylic acids carrying various functionalization on C-7 of their common 3H-spiro[benzofuran-2,1?-cyclohexane] skeleton were synthesized from filifolinol, as analogs of the natural Complement inhibitor K76-COOH. In order to probe the relevance of the C-7 functionalization on their bioactivity, the ability of the analogs to inhibit Complement activation through the classical pathway was determined. The observed results suggest that functionalization of C-7 can modulate the inhibitory activity of the tested compounds. The 7-trifluoromethyl derivative was the compound with the lowest IC50 value among the tested analogs, being more potent than K76-COOH.
publishDate 2012
dc.date.none.fl_str_mv 2012-09
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/11336/105021
Larghi, Enrique Leandro; Operto, María Alejandra; Torres, Nelson René; Kaufman, Teodoro Saul; Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 55; 9-2012; 74-84
0223-5234
CONICET Digital
CONICET
url http://hdl.handle.net/11336/105021
identifier_str_mv Larghi, Enrique Leandro; Operto, María Alejandra; Torres, Nelson René; Kaufman, Teodoro Saul; Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 55; 9-2012; 74-84
0223-5234
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.ejmech.2012.07.003
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0223523412004151
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 Elsevier France-editions Scientifiques Medicales Elsevier
publisher.none.fl_str_mv Elsevier France-editions Scientifiques Medicales 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
_version_ 1844613056777158656
score 13.070432

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