Green one-pot synthesis of quinoxaline derivatives using sulfo-anthranilic acid functionalized alginate-MCFe2O4 nanostructures: a novel superparamagnetic catalyst with antiproliferative potential

Abstract

This study reports a green, multi-component synthesis of 2-aminoimidazole–linked quinoxaline Schiff bases using a novel superparamagnetic acid catalyst. The catalyst consists of sulfo-anthranilic acid (SAA) immobilized on MnCoFe₂O₄@alginate magnetic nanorods (MNRs), achieving high SAA loading (1.8 mmol g⁻¹) and product yields (91–97%). Characterization of the MCFe₂O₄@Alginate@SAA MNR catalyst revealed an inverse spinel structure (XRD), a saturation magnetization of 31 emu g⁻¹ (VSM), 17.5% organic content (TGA), and a rod-like morphology with diameters of 30–60 nm and lengths of 150–250 nm (SEM). Elemental composition confirmed by EDX analysis indicated successful SAA immobilization and high catalyst purity. The synthesized quinoxaline derivatives were evaluated for antiproliferative activity against SKOV3 and HCT-116 cancer cell lines using the MTT assay. Several compounds, notably 4a, 4s, 4t, 4w, and 4x, exhibited potent activity, inhibiting HCT-116 proliferation by >50% at 50 μg mL⁻¹. Compound 4a demonstrated the most significant inhibition, with 82.3% against SKOV3 cells after 48 h and 69.0% against HCT-116 cells after 24 h, both at 50 μg mL⁻¹. These results suggest the potential of 2-aminoimidazole–linked quinoxaline Schiff bases, particularly 4a, as promising multi-target chemotherapy agents.