Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins

ABSTRACT: A series of styrylcoumarins were obtained via Mizoroki-Heck reactions between 3-bromo-4-methyl-7-(octyloxy)-2H-chromen-2-one or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate and functionalized styrenes. The structures of the products were elucidated by spectroscopic analysis. All compoun...

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Autores:
Herrera Ramírez, Angie Zulema
Castrillón López, Wilson Andrés
Otero Tejada, Elver Luis
Ruíz Agudelo, Esneyder
Carda Usó, Pedro Miguel
Agut Montoliu, Raül
Naranjo Preciado, Tonny Williams
Moreno Quintero, Gustavo Alberto
Maldonado Celis, María Elena
Cardona Galeano, Wilson
Tipo de recurso:
Article of investigation
Fecha de publicación:
2018
Institución:
Universidad de Antioquia
Repositorio:
Repositorio UdeA
Idioma:
eng
OAI Identifier:
oai:bibliotecadigital.udea.edu.co:10495/20370
Acceso en línea:
http://hdl.handle.net/10495/20370
https://link.springer.com/article/10.1007/s00044-018-2202-0
Palabra clave:
Coumarins
Cumarinas
Colorectal Neoplasms
Neoplasias Colorrectales
Styrylcoumarin
Antiproliferative activity
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc-sa/2.5/co/
id UDEA2_dc4ebc4e0bba4ddae50f6a5288414fe3
oai_identifier_str oai:bibliotecadigital.udea.edu.co:10495/20370
network_acronym_str UDEA2
network_name_str Repositorio UdeA
repository_id_str
dc.title.spa.fl_str_mv Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
title Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
spellingShingle Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
Coumarins
Cumarinas
Colorectal Neoplasms
Neoplasias Colorrectales
Styrylcoumarin
Antiproliferative activity
title_short Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
title_full Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
title_fullStr Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
title_full_unstemmed Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
title_sort Synthesis and Antiproliferative Activity of 3 and 7-Styrylcoumarins
dc.creator.fl_str_mv Herrera Ramírez, Angie Zulema
Castrillón López, Wilson Andrés
Otero Tejada, Elver Luis
Ruíz Agudelo, Esneyder
Carda Usó, Pedro Miguel
Agut Montoliu, Raül
Naranjo Preciado, Tonny Williams
Moreno Quintero, Gustavo Alberto
Maldonado Celis, María Elena
Cardona Galeano, Wilson
dc.contributor.author.none.fl_str_mv Herrera Ramírez, Angie Zulema
Castrillón López, Wilson Andrés
Otero Tejada, Elver Luis
Ruíz Agudelo, Esneyder
Carda Usó, Pedro Miguel
Agut Montoliu, Raül
Naranjo Preciado, Tonny Williams
Moreno Quintero, Gustavo Alberto
Maldonado Celis, María Elena
Cardona Galeano, Wilson
dc.subject.decs.none.fl_str_mv Coumarins
Cumarinas
Colorectal Neoplasms
Neoplasias Colorrectales
topic Coumarins
Cumarinas
Colorectal Neoplasms
Neoplasias Colorrectales
Styrylcoumarin
Antiproliferative activity
dc.subject.proposal.spa.fl_str_mv Styrylcoumarin
Antiproliferative activity
description ABSTRACT: A series of styrylcoumarins were obtained via Mizoroki-Heck reactions between 3-bromo-4-methyl-7-(octyloxy)-2H-chromen-2-one or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate and functionalized styrenes. The structures of the products were elucidated by spectroscopic analysis. All compounds were evaluated against SW480 and CHO-K1 cell lines. A number of hybrids showed good antiproliferative activity. Among the tested compounds, hybrids 6e, 10c and 10d, exhibited the highest activity (IC50- SW480/48h = 6,92; 1,01 and 5,33 μM, respectively) and selectivity (IS48h = >400; 67,8 and 7,2, respectively). In addition, these compounds were able to preserve their activities over time. The results achieved by these hybrids were even better than the lead compounds (coumarin and resveratrol) and the standard drug (5-FU). As regards structure-activity relationship it seems that the location of the styryl group on the coumarin structure and the presence of the hydroxyl group on the phenyl ring were determinant for the activity.
publishDate 2018
dc.date.issued.none.fl_str_mv 2018
dc.date.accessioned.none.fl_str_mv 2021-06-25T02:43:33Z
dc.date.available.none.fl_str_mv 2021-06-25T02:43:33Z
dc.type.spa.fl_str_mv info:eu-repo/semantics/article
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dc.type.local.spa.fl_str_mv Artículo de investigación
format http://purl.org/coar/resource_type/c_2df8fbb1
status_str publishedVersion
dc.identifier.issn.none.fl_str_mv 1054-2523
dc.identifier.uri.none.fl_str_mv http://hdl.handle.net/10495/20370
dc.identifier.doi.none.fl_str_mv 10.1007/s00044-018-2202-0
dc.identifier.eissn.none.fl_str_mv 1554-8120
dc.identifier.url.spa.fl_str_mv https://link.springer.com/article/10.1007/s00044-018-2202-0
identifier_str_mv 1054-2523
10.1007/s00044-018-2202-0
1554-8120
url http://hdl.handle.net/10495/20370
https://link.springer.com/article/10.1007/s00044-018-2202-0
dc.language.iso.spa.fl_str_mv eng
language eng
dc.relation.ispartofjournalabbrev.spa.fl_str_mv Med. Chem. Res.
dc.rights.spa.fl_str_mv info:eu-repo/semantics/openAccess
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by-nc-sa/2.5/co/
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dc.rights.creativecommons.spa.fl_str_mv https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/2.5/co/
http://purl.org/coar/access_right/c_abf2
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dc.format.extent.spa.fl_str_mv 25
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv Springer
dc.publisher.group.spa.fl_str_mv Impacto de Componentes Alimentarios en la Salud
Micología Médica y Experimental
Química de Plantas Colombianas
dc.publisher.place.spa.fl_str_mv Cambridge, Inglaterra
institution Universidad de Antioquia
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spelling Herrera Ramírez, Angie ZulemaCastrillón López, Wilson AndrésOtero Tejada, Elver LuisRuíz Agudelo, EsneyderCarda Usó, Pedro MiguelAgut Montoliu, RaülNaranjo Preciado, Tonny WilliamsMoreno Quintero, Gustavo AlbertoMaldonado Celis, María ElenaCardona Galeano, Wilson2021-06-25T02:43:33Z2021-06-25T02:43:33Z20181054-2523http://hdl.handle.net/10495/2037010.1007/s00044-018-2202-01554-8120https://link.springer.com/article/10.1007/s00044-018-2202-0ABSTRACT: A series of styrylcoumarins were obtained via Mizoroki-Heck reactions between 3-bromo-4-methyl-7-(octyloxy)-2H-chromen-2-one or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate and functionalized styrenes. The structures of the products were elucidated by spectroscopic analysis. All compounds were evaluated against SW480 and CHO-K1 cell lines. A number of hybrids showed good antiproliferative activity. Among the tested compounds, hybrids 6e, 10c and 10d, exhibited the highest activity (IC50- SW480/48h = 6,92; 1,01 and 5,33 μM, respectively) and selectivity (IS48h = >400; 67,8 and 7,2, respectively). In addition, these compounds were able to preserve their activities over time. The results achieved by these hybrids were even better than the lead compounds (coumarin and resveratrol) and the standard drug (5-FU). As regards structure-activity relationship it seems that the location of the styryl group on the coumarin structure and the presence of the hydroxyl group on the phenyl ring were determinant for the activity.COL0015329COL0013709COL008381125application/pdfengSpringerImpacto de Componentes Alimentarios en la SaludMicología Médica y ExperimentalQuímica de Plantas ColombianasCambridge, Inglaterrainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARTArtículo de investigaciónhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/2.5/co/http://purl.org/coar/access_right/c_abf2https://creativecommons.org/licenses/by-nc-sa/4.0/Synthesis and Antiproliferative Activity of 3 and 7-StyrylcoumarinsCoumarinsCumarinasColorectal NeoplasmsNeoplasias ColorrectalesStyrylcoumarinAntiproliferative activityMed. Chem. Res.Medicinal Chemistry Research18931905271CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-81051http://bibliotecadigital.udea.edu.co/bitstream/10495/20370/2/license_rdfe2060682c9c70d4d30c83c51448f4eedMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://bibliotecadigital.udea.edu.co/bitstream/10495/20370/3/license.txt8a4605be74aa9ea9d79846c1fba20a33MD53ORIGINALHerreraAngie_2018_SynthesisAntiproloferativeStyrylcoumarins.pdfHerreraAngie_2018_SynthesisAntiproloferativeStyrylcoumarins.pdfArtículo de investigaciónapplication/pdf542703http://bibliotecadigital.udea.edu.co/bitstream/10495/20370/1/HerreraAngie_2018_SynthesisAntiproloferativeStyrylcoumarins.pdfffb09727a2a902a3e4abbbe1da1e9fccMD5110495/20370oai:bibliotecadigital.udea.edu.co:10495/203702022-05-27 12:53:03.762Repositorio Institucional Universidad de Antioquiaandres.perez@udea.edu.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