Ethyl 2-(4-methoxyphenyl)-3-(thiophene-2-carbonyl)cyclopropanecarboxylates 2(a-f) and ethyl 4-aryl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylates 4(a-f) were synthesized by simple procedure. The synthesized new compounds were screened in vitro for their antimicrobial and antioxidant activities. The compounds 2b and 4f showed excellent antibacterial activity; while 2b and 4f showed remarkable antifungal properties. The results of antioxidant activity studies revealed that compounds 4b and 4f manifested profound antioxidant potential. The docking studies were done for the final compounds. The ADME result indicates that all these molecules possess pharmaceutical properties in the range of 95% of drugs.