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A series of novel chroman scaffold incorporate spirochromanone derivatives were synthesized from 2-hydroxyacetophenone and cyclic alkanones under microwave irradiation in good yields. Newly synthesized compounds were characterized by analytical and spectral (IR, proton nuclear magnetic resonance, ¹³C nuclear magnetic resonance, and mass spectrometry) methods. The synthesized compounds were evaluated for their antioxidant and anti-inflammatory activities and were compared with standard drugs. Among all the synthesized compounds 3d (6.09), 3g (5.32), 3h (2.03), 4a (1.17), 4b (0.50), 4c (6.59), 4d (7.86), 4e (6.85), 4f (4.82), and 4g (6.59) were exhibited higher antioxidant activity comparable to that of ascorbic acid (IC₅₀ 8.64 µM). The compounds 3a, 3b, 3c, 4c, and 4d were found to have good anti-inflammatory activity. The binding mode of the titled compounds has been proposed …