The study was aimed to evaluate the invitro cytotoxicity of Flavanone derivatives namely 3–[4–(benzyloxy)–phenyl]–2,3–dihydro–1H–benzo[f]–chromen–1–one– (BDBC) and  (3–(4–methoxyphenyl)–2,3–dihydro–1H–naphtho[2,1–b]pyran–1–one – (MDNP) which were synthesized  and their cytotoxicity against normal Vero cell and breast cancer MCF7 cell lines were assessed by MTT assay method. Higher IC₅₀ values of the compounds with the Vero cell line suggest that they are widely non– toxic. The IC₅₀ values of 15.6 and               31. 2 μg/ml, exhibited against the MCF7 cells by the derivatives, BDBC and MDNP suggest the significant anticancer activity of the compounds. Molecular docking studies were performed in order to validate the obtained biological results. Induced fit docking analysis shows that the exemestane (co–crystal) has docked well at the active site of target protein with the glide score of –9.473 and glide energy of –48.055 Kcal/mol. The compounds BDBC and MDNP have been observed to be at the active site of target protein with the glide score of –8.228, –7.952 and glide energy of –55.582, –40.528 Kcal/mol, respectively, which are comparable with the corresponding values of the co–crystal.