Commercial Copper-Catalyzed Aerobic Oxidative Synthesis of 4H-3,1-Benzoxazine and Their Effects on Anti-Inflammatory Genes Expression

A facile green synthesis of the anti-inflammatory gene expression of 4H-3,1-benzoxazine was developed under a commercial copper catalytic system. Benzoxazines were synthesized from 2-aminobenzyl alcohols and aromatic aldehydes including heterocyclic aromatic aldehydes using an economical commercially available copper(I)iodide (CuI) as a catalyst in the presence of the base, ^tBuOK. Target products were achieved in moderate to high yields with up to 75 % isolated yield. 4H-3,1-Benzoxazine enabled down-regulation of inflammatory gene expression including tumor necrosis factor-α (TNF-α), inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and interleukin-1β (IL-1β) in the lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cell line using a real-time quantitative polymerase chain reaction (RT-qPCR) comparable to anti-inflammatory drug, dexamethasone. These results demonstrated that 4H-3,1-Benzoxazines possess the potential capability of anti-inflammation.