Suzuki coupling-based synthesis and in vitro cytotoxic evaluation of C-2 aryl derivatives of Withaferin A

•A simple and efficient protocol for the α-halogenation of ring A of withaferin A followed by palladium-mediated coupling of 2-iodowithaferin A with boronic acids leads to the generation of 2-aryl withaferin A analogs.•A series of 18 new 2-aryl analogs of withaferin A have been synthesized and evaluated for their anticancer potential against four cell lines.•One of the newly generated derivative, 2-(4-bromophenyl)-withaferin A (9) showed ≥ 50 % growth inhibition against all the tested cell lines at 10 μM concentration with an IC50 of 6.6 ± 0.8 against triple-negative breast cancer cell line MDA-MB-231.•Compound 9 implicated suppression of cellular proliferation, colony formation, cell migration and cell invasion in TNBC cells.•Cell cycle analysis showed that compound 9 arrests G1 phase of cell cycle in triple negative breast cancer cells MDA-MB-231.