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The discovery of C-3 tethered 2-oxo-benzo[1,4]oxazines as potent antioxidants is disclosed. All the analogs  20a-20ab  have been synthesized via “on water” ultrasound-assisted irradiation conditions in excellent yields (upto 98%). All the compounds have been evaluated for their  in vitro  antioxidant activities using DPPH free radical scavenging assay as well as FRAP assay. The result showed promising antioxidant activities having IC 50  values in the range of 4.74 ± 0.08 to 92.20 ± 1.54 μg/mL taking ascorbic acid (IC 50  = 4.57 μg/mL) as standard reference. In this study, compounds  20b  and  20t , the most active compound of the series, showed IC 50  values of 6.89 ± 0.07 μg/mL and 4.74 ± 0.08 μg/mL, respectively in comparison with ascorbic acid. In addition, the detailed SAR study shows that electron-withdrawing group increases antioxidant activity and vice versa. Furthermore, in the FRAP assay, eight compounds ( 20c ,  20j ,  20m ,  20n ,  20r ,  20u ,  20z , and  20aa ) were found more potent than standard reference BHT (C 0.5FRAP  = 546.0 ± 13.6 μM). The preliminary cytotoxic study reveals the non-toxic nature of active compounds  20b  and  20t  in non-cancerous 3T 3  fibroblast cell lines in MTT assay up to 250 μg/mL concentration. The results were validated  via  carrying out  in silico  molecular docking studies of promising compounds  20a ,  20b , and  20t  in comparison with standard reference. To the best of our knowledge, this is the first detailed study of C-3 tethered 2-oxo-benzo[1,4]oxazines as potential antioxidant agents.

frontiers in chemistry

Discovery of C-3 Tethered 2-oxo-benzo[1,4]oxazines as Potent Antioxidants: Bio-Inspired Based Design, Synthesis, Biological Evaluation, Cytotoxic, and in Silico Molecular Docking Studies