Green one-pot synthesis of quinoxaline derivatives using sulfo-anthranilic acid functionalized alginate-MCFe(2)O(4) nanostructures: a novel superparamagnetic catalyst with antiproliferative potential

利用磺基邻氨基苯甲酸功能化的藻酸盐-MCFe(2)O(4)纳米结构,绿色一锅法合成喹喔啉衍生物:一种具有抗增殖潜力的新型超顺磁性催化剂

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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 MnCoFe(2)O(4)@alginate magnetic nanorods (MNRs), achieving high SAA loading (1.8 mmol g(-1)) and product yields (91-97%). Characterization of the MCFe(2)O(4)@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.

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