The present investigation is concerned with synthesis of new 2 and 6 - substituted 4H-chromen-4-One derivatives with the objectives of discovering novel and potent anti-inflammatory agents and anti-oxidants. The results of anti-inflammatory activity were revealed that the compound has indole 2 substitution with 4-nitrophenyl amino methyl (at 6th position) on 4H- chromen-4-one having more anti-inflammatory activity as compared to other substituents. While, indole 2 substituted 4-methoxy phenyl amino methyl (at 6th position) 4H-chromen-4-one showed outperformed anti-oxidant activity in different anti-oxidant model as compared to other substituents. The all newly synthesized compounds displayed moderate to potent anti-inflammatory and anti-oxidant activity and has therapeutic potential in combating this devastating inflammatory and oxidative condition of the body, might be deserve promising substances for further in vivo evaluation as anti-inflammatory and anti-oxidant properties. However the anti-inflammatory activity is not related to antioxidant potential.