Cancer is a major public health concern worldwide and the second leading cause of death after cardio vascular diseases. as per who and globocan reports of more and less developed regions of the world, breast cancer is the most common type of cancer in women among the other types of cancer. as per pbcr (population based cancer registry) data, breast cancer accounts for 25% to 32% of all female cancers across india. the biology of breast carcinoma is complex with multiple factors contributing to its initiation and progression and these include steroid receptors [estrogen receptor (er), progesterone receptor (pgr), retinoic acid receptor (rar-β)) and selected suppressor/susceptibility genes (p53, brca1, brca2)]. among them approximately 70-80% of breast tumors are er positive (er+). aromatase is an enzyme that plays a critical role in the development of er positive (er+) breast cancer. as aromatase catalyses the aromatization of androstenedione to estrone, it is a promising target for therapeutic management of breast cancer. many natural and synthetic flavonoids have been studied and reported for their anti-cancer activity against breast carcinoma by inhibition of aromatase enzyme. the flavonoid skeleton mimics the steroidal moiety and some of marketed aromatase inhibitors having steroid moiety include exemestane, testolactone and formestane. hence, a series of flavonoids and benzoflavones have been designed by sar pattern of flavonoids derived from literature and molecular docking study. out of 76 designed compounds 40 flavanoids were synthesized and their in-silico admet properties were predicted. the physicochemical properties and % yield of flavonoids were determined. the % yield of all synthesized flavonoids were in the range of 49 - 94%. the characterization of synthesized flavonoid derivatives was done by various spectroscopic techniques like ir, mass and 1h-nmr. the potential activity of selected compounds based on docking score were evaluated by cytotoxicity assay in mcf-7 (human breast cancer cell line). among them, compounds 6b, 2k, 4k, 6k, 4b, 2b and 4c displayed potent anti-proliferative activity with ic50 values of 0.35 μm, 1.64 μm, 15.75 μm, 16.08 μm, 16.08 μm, 20.73 μm and 22.02 μm respectively compared to standard drug letrozole (30.39 µm). further, 06 compounds namely 2b, 2k, 6b, 6k, 4b and 4k were selected for in-vitro aromatase inhibitory activity by fluorogenic kit method. the % inhibition of test compounds and standard drug (letrozole) were measured at three different concentration 0.1, 1.0 and 10.0 µm. the ic50 value of test and standard compounds were measured. among them compounds 2b (2-(3-hydroxyphenyl)4h-chromen-4-one) and 6b (2-(3-hydroxyphenyl)-4h-benzo[h]chromen-4-one) were found to be most potent flavonoids with ic50 values of 0.31 µm and 0.36 µm compared to standard drug letrozole (0.86µm). while the other compounds 2k, 4b, 6k and 4k were considered to have comparable activity with respect to letrozole based on their ic50 values of 2k (0.93 µm), 4b (0.98 µm), 6k (1.06 µm) and 3.06 µm (4k) respectively. their considerable aromatase inhibitory activities makes them a good candidate for the development of aromatase inhibitors.