Synthesis and cytotoxic activities of C-benzylated flavonoids.

Arch Pharm Res

College of Pharmacy, Sookmyung Women's University, Seoul, 140-742, Korea.

Published: January 2009

AI Article Synopsis

  • Some C-benzylated flavonoids based on gericudranin A were synthesized to study their cytotoxic effects and understand their structure-activity relationships.
  • The synthesis involved converting 2,4,6-trihydroxyacetophenone into target compounds through a series of chemical steps, including protection, aldol condensation, cyclization, and more.
  • Among the synthesized compounds, 5b exhibited the strongest cytotoxicity, particularly against the SNB19 cancer cell line, demonstrating effectiveness similar to adriamycin with an IC(50) value of 0.7 microM.

Article Abstract

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.

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http://dx.doi.org/10.1007/s12272-009-1118-0DOI Listing

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