4H-Chromene derivatives are an important scaffold in organic and medicinal chemistry. They belong to the class of naturally occurring benzopyran derivatives with a wide range of biological applications, such as anti-inflammatory, antioxidant, anticancer, antiviral and potent apoptosis inducers. The two selected 4-phenyl-4H-chromene derivatives were subjected to in silico molecular modelling studies. The compound were synthesized by the three component one-pot reaction of appropriate 4-bromobenzaldehyde, malononitrile and substituted phenol. The synthesis of the two derivatives were based on the Knoevenagel condensation and Michael addition. The synthesized compounds were characterized by melting point, TLC, IR and screened for their in vitro antioxidant and anti-inflammatory activities. This study revealed that these synthesized derivatives tends to have good activity against TNF- α mediated diseases and thus their reduce inflammation and pain because of its anti-inflammatory and anti- oxidant activity.