Synthesis, structural characterization, antioxidant and cytotoxic activity towards human cancer cell lines and computational studies of new Ni(II), Co(II) and Pd(II) complexes with 3-[bis(3,5-dimethylpyrazol-1-yl)methyl]chromen-4-one derivatives

Abstract Synthetic derivatives of flavonoids are a promising class of biologically active compounds. Here we report a family of (chromon-3-yl)-bis(3,5-dimethylpyrazol-1-yl)methanes bearing various substituents in chromone fragment. They have been studied for the antioxidant activity and spectra of their biological activity have been predicted. New Ni(II), Co(II) and Pd(II) complexes, supported by 3-[bis(3,5-dimethylpyrazol-1-yl)methyl]-6-fluoro-chromen-4-one, have been synthesized and characterized using 1H NMR, high-resolution MALDI-TOF spectrometry and elemental analyses. The molecular structures of 3-[bis(3,5-dimethylpyrazol-1-yl)methyl]-chromen-4-one 1, 3-[bis(3,5-dimethylpyrazol-1-yl)methyl]-6-chloro-chromen-4-one 7 and Co dichloride complex with 3-[bis(3,5-dimethylpyrazol-1-yl)methyl]-6-fluoro-chromen-4-one 15 have been determined using single crystal X-ray diffraction studies. The cytotoxic activity of metal complexes and the ligand 1 has been studied on 4 cell lines of different histological origin. It has been observed that Ni complex exhibits higher cytotoxicity against breast cancer cells MCF7 and Co complex has almost the same effect on the growth of all studied tumor cells.