A series of ethyl 2-(2-cyano-3-(substituted phenyl)acrylamido)-4,5,6,7- tetrahydrobenzo[b]thiophene-3-carboxylates were prepared by knoevenagel condensation of active methylene group of ethyl 2-(2-cyanoacetamido)- 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate with substituted benzaldehydes in toluene containing catalytic amounts of glacial acetic acid and piperidine. All the compounds were purified by recrystallization from suitable solvent and characterized by spectral and analytical methods. The antioxidant properties and antibacterial effects of the synthesized compounds were studied. Among the series, compounds with 4-hydroxy substituent on phenyl ring exhibited greater antioxidant activity at 100 µM concentration. The results of antibacterial activity revealed that 4-dimethyl amino derivative exhibited highest activity against B. subtilis, E.coli and S. aureus