Apigenin Bioisosteres: Synthesis and Evaluation of their Antioxidant, Antimicrobial, and Anticancer Activities

: A novel series of Apigenin bioisosteres [1(4-chlorophenyl)-3-phenyl prop-2-ene-1-one] non-cyclic derivatives (4a-4c) and [7-hydroxy-2-phenyl-4H-chromen-4-one] cyclic derivatives (9a- 9d) were synthesized. The newly synthesized apigenin bioisosteres were confirmed using UV, IR, NMR, and mass spectroscopic methods. The antioxidant, antibacterial, and anti-cancer activities of all newly synthesized compounds were assessed using the DPPH free radical scavenging capacity, disc diffusion method, and in vitro MTT assay on the human breast cancer MCF-7 cell line. Almost all the synthesized apigenin bioisosteres had greater antioxidant and antimicrobial activity than standard Apigenin. Out of seven compounds (4a-4c and 9a-9d), five compounds were found to exhibit notable antiproliferative activity on the breast cancer cell line (MCF-7), whereas two compounds, 9c and 9d, did not show notable activity. Our analysis suggests that synthesized Apigenin bioisosteres function as prospective antioxidant, antimicrobial, and anticancer agents.