Coumarin Schiff bases (1-14) synthesized by microwave irradiation method, were evaluated by insilico techniques and for their antioxidant activity by ferric reducing antioxidant power (FRAP) assay. The results from insilico techniques showed that all the compounds exhibit drug likeness satisfying Lipinski rule of five having the ability to behave as drugs. These findings revealed that they are active nuclear receptor, GPCR ligand and enzyme inhibitors. Insilico OSIRIS predictions indicate that all the compounds suffer from teratogenic effect, compounds 9, 14 possesses mutagenic toxicity. OCHEM results clearly indicate that they are inhibitors of CYP1A2 a subtype of cytochrome P450. Compound 8 gave FRAP value nearer to the standard. The study provides a good scope for further development of novel targeted molecules.