In search of molecules that possess biological activity, synthesis of novel pyrrolidines chalcones (AP-JP) obtained by condensing different aldehydes with diazotized 4-amino acetophenone coupled to pyrrolidine and evaluate them for in vitro anticancer, anti-inflammatory and antibacterial activities was undertaken. The synthesized compounds were screened for anticancer activity against human breast cancer cell lines- MCF-7 and MDA-MB-468. In vitro methods for anti-inflammatory activity like inhibition of bovine albumin denaturation and heat induced hemolysismethod was used.Antibacterial and antitubercular activities were also performed.The structures of synthesized compounds were confirmed based on the IR, 1H NMR and mass spectral data.Among the synthesized compounds, 3IP shown IC50 value of 25-30 μg against MCF-7 cell line, whereas 3FP shown IC50 value of 25 μg against MDA-MB-468 cell lines.Compound 3GP has moderate anti inflammatory activity in bovine denaturation and heat induced hemolytic method.Compounds 3BP, 3CP and 3DP shown MIC of 0.025μg/ml against Staphylococcus aureus, while compounds 3AP and 3IP shown MIC of 0.025μg/ml against E. faecalis. 3CP is sensitive to mycobacterium tuberculosis with a MIC of 6.25 μg/ml.