Design, synthesis and biological evaluation of chrysin long-chain derivatives as potential anticancer agents.

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Lv PC, Wang KR, Li QS, Chen J, Sun J, Zhu HL

Design, synthesis and biological evaluation of chrysin long-chain derivatives as potential anticancer agents.

Bioorg Med Chem. 2010 Feb;18(3):1117-23. doi: 10.1016/j.bmc.2009.12.048. Epub 2009 Dec 24.

PubMed ID

20056425 [ View in PubMed

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Abstract

A series of long-chain derivatives of chrysin (compounds 3-22) were synthesized to evaluate for their antiproliferative activities against the human liver cancer cell line HT-29 and EGFR inhibitory activity. Among the compounds tested, compounds hexadecyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetate (10) and N-hexadecyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetamide (20) displayed potent EGFR inhibitory activity with IC(50) values of 0.048 microM and 0.035 microM), comparable to the positive control erlotinib. Docking simulation of compounds 10 and 20 was carried out to illustrate the binding mode of the molecular into the EGFR active site, and the result suggested that compound 10 and 20 can bind the EGFR kinase well. Thus, compounds 10 and 20 with potent EGFR inhibitory activity would be potential anticancer agents.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Gefitinib	Epidermal growth factor receptor	IC 50 (nM)	33	N/A	N/A	Details