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/
Description
Summary: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.