Synthesis and cytotoxic activities of C-benzylated flavonoids.
Some C-benzylated flavonoids based on gericudranin A were synthesized and evaluated their cytotoxic activities for the elucidation of structure-activity relationship. 2,4,6-Trihydroxyacetophenone was converted to target molecules in 6 approximately 7 steps via sequential protection, aldol condensation, cyclization, regioselective C-benzylation, and deprotection. The cellular growth inhibition of the synthetic C-benzylated flavonoids was investigated against sixteen human cancer cell lines. Among these compounds, 5b showed the most potent cytotoxicities against several cell lines, especially as potent as adriamycin against SNB19 cell lines with an IC(50) value of 0.7 microM.
Choi
Yoon-Jung
YJ
College of Pharmacy, Sookmyung Women's University, Seoul, 140-742, Korea.
Kim
Hwan Mook
HM
Kim
Hee-Doo
HD
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D011794:Quercetin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; C098271:gericudranin A; D011794:Quercetin