Synthesis and cytotoxic evaluation of protoanemonin and three brominated derivatives

Synthesis and cytotoxic evaluation of protoanemonin and three brominated derivatives

The protoanemonin, a natural furanone, was synthesized from (Z)-4-bromo-5-(bromomethylene)-furan-2(5H)-one by a reductive dehalogenation reaction with zinc. The 5-(dibromomethylene)-2(5H)-furanone and (E)-5-(bromomethylene)-2(5H)-furanone were also synthetized from levulinic acid bromination and aci...

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Bibliographic Details
Published in:Revista colombiana de química Vol. 49; no. 3; pp. 13 - 18
Main Authors: Villegas Pañeda, Alejandra Guadalupe, Ramírez Apan, María Teresa Obdulia
Format: Journal Article
Language:English
Published: Bogota Universidad Nacional de Colombia 01-01-2020
Subjects:
Acids
Bromination
Bromine
Cancer
Cell cycle
Chromatography
Cytotoxicity
Levulinic acid
NMR
Nuclear magnetic resonance
Synthesis
Zinc
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Summary:The protoanemonin, a natural furanone, was synthesized from (Z)-4-bromo-5-(bromomethylene)-furan-2(5H)-one by a reductive dehalogenation reaction with zinc. The 5-(dibromomethylene)-2(5H)-furanone and (E)-5-(bromomethylene)-2(5H)-furanone were also synthetized from levulinic acid bromination and acid promoted cyclization. The antiproliferative activity of all synthesized compounds against the human cancer cell lines PC-3 (prostate) and U-251 (glioblastoma) was investigated. The results showed that all the obtained furanones are more active than the reference drug cisplatin, with IC50 values in the range of 0.31 ± 0.02 to 7.30 ± 0.08 μM. However, (E)-5-(bromomethylene)-2(5H)-furanone, with a bromine atom in the double bond, was the most active, and demonstrated to be about 25-fold more active than the reference drug cisplatin.
ISSN:0120-2804
2357-3791
DOI:10.15446/rcq.v49n3.87159