TY - JOUR
T1 - Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins
AU - Herrera-R, Angie
AU - Castrillón, Wilson
AU - Otero, Elver
AU - Ruiz, Esneyder
AU - Carda, Miguel
AU - Agut, Raúl
AU - Naranjo, Tonny
AU - Moreno, Gustavo
AU - Maldonado, Maria Elena
AU - Cardona-G, Wilson
N1 - Publisher Copyright:
© 2018, Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2018/8/1
Y1 - 2018/8/1
N2 - 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.
AB - 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.
KW - Antiproliferative activity
KW - Colorectal cancer
KW - Coumarin
KW - Hybrids
KW - Styrylcoumarin
UR - http://www.scopus.com/inward/record.url?scp=85048747308&partnerID=8YFLogxK
U2 - 10.1007/s00044-018-2202-0
DO - 10.1007/s00044-018-2202-0
M3 - Artículo en revista científica indexada
AN - SCOPUS:85048747308
SN - 1054-2523
VL - 27
SP - 1893
EP - 1905
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
IS - 8
ER -