Design, synthesis, molecular docking and molecular dynamics studies of some 3-methoxy flavone derivatives as an anti-breast cancer agent
Abstract
Objective: The present study aimed to synthesize flavone hybrids with 3-methoxy substitution and an N-heterocyclic ring at the 4' position of the flavone B ring and test their effectiveness against cancer.
Method: Molecular docking of 3-methoxy flavone was studied on ER-α and EGFR. By cyclizing chalcones, various flavonol derivatives were synthesized and 3-methoxy flavones were produced by flavonol methylation. 3-methoxy flavone derivatives substituted with various heterocyclic rings like morpholine, piperidine, N-methyl piperazine, pyrrolidine, triazole, imidazole, and benzimidazole were synthesized. 1HNMR, 13CNMR, IR, and mass spectra verified all compound's structures. 3-methoxy flavone derivatives evaluated for their anticancer potential by MTT assay and SRB assay on breast cancer (MCF-7 and MDA-MB-231). The molecular dynamics simulation was also studied for active compounds on the human estrogen receptor alpha and epidermal growth factor receptor.
Results: 3-methoxy flavone derivatives were successfully synthesized and evaluated by spectroscopic studies. The MTT assay on MCF-7 cell lines revealed significant cytotoxic activity of compounds Ciii and Civ by expressing IC50 values of 13.08 ± 1.80 and 20.3 ± 1.47 µg/ml, respectively. The SRB assay on MDA-MB-231 showed a potent response by compounds Cii, Cv & Cvi with IC50 values of 5.54 ± 1.57, 5.44 ± 1.66 and 8.06 ± 1.83 µg/ml, respectively. Overall results showed the effective substitution of 3-methoxy flavone was…
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