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...
- 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/
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UDEA2 |
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Repositorio UdeA |
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|
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 |
dc.type.coarversion.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
dc.type.hasversion.spa.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.coar.spa.fl_str_mv |
http://purl.org/coar/resource_type/c_2df8fbb1 |
dc.type.redcol.spa.fl_str_mv |
https://purl.org/redcol/resource_type/ART |
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/ |
dc.rights.accessrights.spa.fl_str_mv |
http://purl.org/coar/access_right/c_abf2 |
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 https://creativecommons.org/licenses/by-nc-sa/4.0/ |
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 |
bitstream.url.fl_str_mv |
http://bibliotecadigital.udea.edu.co/bitstream/10495/20370/2/license_rdf http://bibliotecadigital.udea.edu.co/bitstream/10495/20370/3/license.txt http://bibliotecadigital.udea.edu.co/bitstream/10495/20370/1/HerreraAngie_2018_SynthesisAntiproloferativeStyrylcoumarins.pdf |
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bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Repositorio Institucional Universidad de Antioquia |
repository.mail.fl_str_mv |
andres.perez@udea.edu.co |
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1812173172790788096 |
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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 |