5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino) phenyl) oxazolidin-5-yl) methyl) thiophene-2-carboxamide derivatives were synthesized in a simple and efficient approach. Eco-friendly, multi-step synthesis of 2-(oxiran-2-ylmethyl) isoindoline-1,3-dione, 4-(4-aminophenyl) morpholin-3-one, and 5-chlorothiophene-2-carbonyl chloride. Three compounds 3,4, and 7 were designed, prepared and screened for anticancer activity against Hela, MCF- 7, A-549 and K-562 and antibacterial activities against gram +ve and gram vestrains. The carboxamide moieties proved to be capable for the development of new anticancer and anti-bacterial agents. Docking studies carried out on target receptors caspase-3 HeLa cell line and S.aureus DNA-Gyrase also supported the anticancer and antimicrobial activity of compounds 3, 4 and 7.