Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents

Autores
Fortes, Margiani P.; da Silva, Paulo B. N.; Da Silva, Teresinha G.; Kaufman, Teodoro Saul; Militão, Gardenia C. G.; Silveira, Claudio C.
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria; Brasil
Fil: da Silva, Paulo B. N.. Universidade Federal de Pernambuco; Brasil
Fil: Da Silva, Teresinha G.. Universidade Federal de Pernambuco; Brasil
Fil: Kaufman, Teodoro Saul. 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
Fil: Militão, Gardenia C. G.. Universidade Federal de Pernambuco; Brasil
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; Brasil
Materia
3-Thiocyanato-1h-Indoles
Bioactive Heterocycles
Cytotoxic Compounds
Hl60 And Hep-2
Nci-H292 And Mcf-7 Cells
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:11336/52625
Acceder
id CONICETDig_58da852446f70cc62c396178a571d573
oai_identifier_str oai:ri.conicet.gov.ar:11336/52625
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agentsFortes, Margiani P.da Silva, Paulo B. N.Da Silva, Teresinha G.Kaufman, Teodoro SaulMilitão, Gardenia C. G.Silveira, Claudio C.3-Thiocyanato-1h-IndolesBioactive HeterocyclesCytotoxic CompoundsHl60 And Hep-2Nci-H292 And Mcf-7 Cellshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria; BrasilFil: da Silva, Paulo B. N.. Universidade Federal de Pernambuco; BrasilFil: Da Silva, Teresinha G.. Universidade Federal de Pernambuco; BrasilFil: Kaufman, Teodoro Saul. 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; ArgentinaFil: Militão, Gardenia C. G.. Universidade Federal de Pernambuco; BrasilFil: Silveira, Claudio C.. Universidade Federal de Santa Maria; BrasilElsevier France-editions Scientifiques Medicales Elsevier2016-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52625Fortes, Margiani P.; da Silva, Paulo B. N.; Da Silva, Teresinha G.; Kaufman, Teodoro Saul; Militão, Gardenia C. G.; et al.; Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 118; 8-2016; 21-260223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2016.04.039info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523416303324info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-03-31T15:06:58Zoai:ri.conicet.gov.ar:11336/52625instacron: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:34982026-03-31 15:06:58.35CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
title Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
spellingShingle Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
Fortes, Margiani P.
3-Thiocyanato-1h-Indoles
Bioactive Heterocycles
Cytotoxic Compounds
Hl60 And Hep-2
Nci-H292 And Mcf-7 Cells
title_short Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
title_full Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
title_fullStr Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
title_full_unstemmed Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
title_sort Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
dc.creator.none.fl_str_mv Fortes, Margiani P.
da Silva, Paulo B. N.
Da Silva, Teresinha G.
Kaufman, Teodoro Saul
Militão, Gardenia C. G.
Silveira, Claudio C.
author Fortes, Margiani P.
author_facet Fortes, Margiani P.
da Silva, Paulo B. N.
Da Silva, Teresinha G.
Kaufman, Teodoro Saul
Militão, Gardenia C. G.
Silveira, Claudio C.
author_role author
author2 da Silva, Paulo B. N.
Da Silva, Teresinha G.
Kaufman, Teodoro Saul
Militão, Gardenia C. G.
Silveira, Claudio C.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 3-Thiocyanato-1h-Indoles
Bioactive Heterocycles
Cytotoxic Compounds
Hl60 And Hep-2
Nci-H292 And Mcf-7 Cells
topic 3-Thiocyanato-1h-Indoles
Bioactive Heterocycles
Cytotoxic Compounds
Hl60 And Hep-2
Nci-H292 And Mcf-7 Cells
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 novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria; Brasil
Fil: da Silva, Paulo B. N.. Universidade Federal de Pernambuco; Brasil
Fil: Da Silva, Teresinha G.. Universidade Federal de Pernambuco; Brasil
Fil: Kaufman, Teodoro Saul. 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
Fil: Militão, Gardenia C. G.. Universidade Federal de Pernambuco; Brasil
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; Brasil
description A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.
publishDate 2016
dc.date.none.fl_str_mv 2016-08
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/11336/52625
Fortes, Margiani P.; da Silva, Paulo B. N.; Da Silva, Teresinha G.; Kaufman, Teodoro Saul; Militão, Gardenia C. G.; et al.; Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 118; 8-2016; 21-26
0223-5234
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52625
identifier_str_mv Fortes, Margiani P.; da Silva, Paulo B. N.; Da Silva, Teresinha G.; Kaufman, Teodoro Saul; Militão, Gardenia C. G.; et al.; Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 118; 8-2016; 21-26
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.2016.04.039
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523416303324
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
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score 12.720982

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