A series of Rhodanine derivatives were synthesized by Knoevenagel condensation. All the synthesized compounds were tested for their in vitro anticancer activity against MCF-7 and BT-474 human breast cancer cell lines. All the synthesized compounds were characterized and screened for their antimicrobial activity against the bacterial and fungal strain. Majority of the compounds showed good to moderate anticancer and antimicrobial activity. Among these compounds, one showed promising activity against gram-positive bacteria B. subtilis and S. aureus when compared with ampicillin. Some of the most potent compounds possessed selective antimicrobial activity.