Synthesis, Characterization of New Ligand Derived from 4-aminoantipyrine and its Complexes with Few Metallic Ions and Evaluation of their Activity as Anticancer

Abstract

A new heterocyclic ligand (LH) derived from 4-aminoantipyrene was prepared through the reaction of 2-mercaptobenzothiazole with 4-amino-antipyrene dissolved in absolute ethanol as the first step to form compound-A, while the second step involved the reaction of O-phenylenediamine with benzil to produce compound -B, the third step involved the reaction of the products of the first and second steps to give the ligand as a final product. Five complexes, Ni (II), Cu (II), Zn(II), Cd (II) and Ag (I) were synthesized from the reaction of the ligand (LH) with its ionic salts. The ligand and its prepared complexes are characterized by proton nuclear magnetic resonance (1H-NMR), fourier-transform infrared spectroscopy (FTIR), UV-vis spectroscopy and X-rays as well as used other techniques such as quantitative analysis of the elements china health and nutrition survey (CHNS), field emission scanning electron microscope (FESEM) as well as molar conductivity and magnetism sensitivity, in addition to measuring melting points. These techniques were used to determine the structures and geometry of the prepared compounds. FTIR spectra showed that the ligand behaves as a tetra-dentate ligand and that the ratio of ligand to metal is (1:1) for all the prepared complexes according to the molar ratio calculations, which were confirmed by quantitative analysis of the elements CHNS and atomic absorption measurements. The molar conductivity results showed that all the non-electrolytic complexes except the zinc (II) and cadmium (II) complexes were ionic in a 1:1 ratio. From the foregoing, it is proved that the complexes have tetrahedral geometry, with the exception of the Ni(II) and Cu(II) complexes, which are octahedral. The anticancer activity of the ligand and its complex with silver was further evaluated using breast cancer cell lines and compared to the normal cell line. The study showed good results by treating infected cells compared to normal cells.