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Synthesis and Structure-activity Relationships of Chalcone Derivatives as Inhibitors of Ovarian Cancer Cell Growth

[ Vol. 14 , Issue. 11 ]

Author(s):

Zachary D. Tucker, Francis J. Barrios and Amanda J. Krzysiak   Pages 1259 - 1266 ( 8 )

Abstract:


Background: Ovarian cancer remains a disease with a poor five year survival rate. As such, novel therapies are needed. Natural chalcones as well as their synthetic derivatives have shown biological activity in a number of areas including the inhibition of cancer cell growth.

Objective: To synthesize a library of chalcone derivatives, including novel structures, and determiner the inhibition of ovarian cancer cell growth and Structure-activity-relationships.

Methods: The Claisen-Schmidt condensation reaction between substituted acetophenones and aromatic aldehydes was used to produce a series of novel chalcones in moderate to excellent yields and good purity. Cellular proliferation of CA-OV3 cells was measured with a MTS assay.

Results: Out of the thirty-four synthesized compounds, eight are new derivatives. The synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation of these β-phenylacrylophenone derivatives in CA-OV3 cells showed interesting antiproliferative activities providing initial structure – activity information.

Conclusion: Fourteen of the thirty-four tested compounds showed significant activity, with several showing near complete inhibition of growth at 100 µM. The structure-activity relationships suggest that modification to the A ring is widely tolerated and that electron-donating modifications to the B ring are beneficial to activity. Electron-withdrawing modifications to the B ring did not show inhibition of cell growth.

Keywords:

Synthesis, chalcones, claisen-schmidt condensation, structure-activity, ovarian cancer, growth inhibition.

Affiliation:

Department of Chemistry and Physics, Faculty of Chemistry, Bellarmine University, Louisville, KY, Department of Chemistry and Physics, Faculty of Chemistry, Bellarmine University, Louisville, KY, Department of Chemistry and Physics, Faculty of Chemistry, Bellarmine University, 2001 Newburg Rd., Louisville, KY

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