Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Abstract

A robust synthesis of magnetic NiFe 2 O 4 nanoparticles via a hydrothermal technique was investigated. The prepared magnetic NiFe 2 O 4 nanoparticles were characterized using powder X-ray diffraction (XRD), scanning electron microscopy, transmission electron microscopy (TEM), high-resolution TEM, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, infrared spectroscopy and vibrating sample magnetometry. XRD and TEM analyses confirmed the formation of single-phase ultrafine nickel ferrite nanoparticles with highly homogeneous cubic shape and elemental composition. Moreover, the prepared magnetic NiFe 2 O 4 nanoparticles were used as an efficient, cheap and eco-friendly catalyst for the Claisen-Schmidt condensation reaction between acetylferrocene and various aldehydes (aromatic and/or heterocyclic) yielding acetylferrocene chalcones in excellent yields, with easy work-up and reduced reaction time. The products were purified via crystallization. The structures of the produced compounds were elucidated using various spectroscopic analyses ( 1 H NMR, 13 C NMR, GC-MS). The catalyst is readily recovered by simple magnetic decantation and can be recycled several times with no discernible loss of catalytic activity. Furthermore, the prepared chalcone derivatives were evaluated for their anti-tumour activity against three human tumour cell lines, namely HCT116 (colon cancer), MCF7 (breast cancer) and HEPG2 (liver cancer), and showed a good activity against colon cancer. Scheme 1. List of aldehyde substrates (2a-m) and chalcone products (3am) with alkyl groups. A. M. Abu-Dief et al. wileyonlinelibrary.com/journal/aoc

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