In this work, acetic acid functionalized poly(4-vinylpyridinum) bromide as a green and reusable catalyst was successfully tested on the synthesis of various bis-coumarins under solvent-free conditions. In addition, antioxidant and anti-inflammatory activities of the synthesized bis-coumarins were in vitro screened by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and formalin-induced edema model system, respectively. Antifungal activity was also evaluated against Fusarium oxysporum. Results showed that the synthesized bis-coumarins studied possess strong antioxidant ( IC50; 0.149 ± 0.005 to 1.348 ± 0.006 mg/ ml) and anti-inflammatory activities in comparison with ascorbic acid and diclofenac as positive controls, respectively. Also, the compounds showed good inhibition activity against Fusarium oxysporum (58 ± 1.4 to 100 ± 0.0%). For their biological activities, the synthesized bis-coumarins may be suggested to apply as biological agents for special use in future.