Two novel isocoumarins 3-2-[(2,6-dichlorophenyl)amino]benzyl-1H-isochromen-1-one and (1-oxo-1H- isochromen-3-yl)methyl 2-(3-((2,6-dichlorophenyl)amino)phenyl)acetate were synthesized using two anti-inflammatory drugs Diclofenac and Aceclofenac by conventional heating. The compounds were prepared by dissolving the starting material of the non steroidal anti-inflammatory drug with THF and the corresponding acid chloride formation is done using thionyl chloride followed by condensation reaction of acid chlorides with homophthalic acid. The synthesized compounds were successfully characterized by FT-IR, Mass, 1H NMR and 13C NMR. The compounds were evaluated for pharmacological studies such as antibacterial, antifungal, antioxidant and in vitro anti-inflammatory. Results showed promising antibacterial activity against Staphylococcus aureus, Bacillus subtilis and antifungal activity against Aspergillus, Alternaria species. Synthesized compounds also showed good antioxidant, in vitro anti-inflammatory activities when compared to that of standard. © 2015 Scientific Publishers. All rights reserved.