Antioxidants are one of a major defense against toxicity caused by free radicals which makes them effective in the prevention and treatment of diseases, like atherosclerosis, stroke, diabetes, Alzheimer's disease and cancer. The present study discusses the design and synthesis of a new series of cycloheptathiophene/ thienopyrimidine derivatives along with their antioxidant biological evaluation. Virtual screening was performed to build a pharmacophore model based on reported natural active antioxidant compound. All resulted outputs were carefully analyzed for the best matched hits. Moreover, molecular docking was done at the active site of tyrosinase as a predictive tool for exploring the biological activity of the targeted compounds. Free radical scavenging activity was measured using DPPH method in reference to Ascorbic acid. Six out of fifteen synthesized compounds showed more significant antioxidant activity than that recorded by the reference standard.