Synthesis, characterization and anticancer activity of new zinc(II), molybdate(II), palladium(II), silver(I), rhodium(III), ruthenium(II) and platinum(II) complexes of 5,6-diamino-4-hydroxy-2-mercaptopyrimidine

Abstract

New complexes of 5,6-diamino-4-hydroxy-2-mercaptopyrimidine (Hdahmp), [Zn(Hdahmp)2Cl2], [Zn(bpy)(dahmp)]Cl, [Zn(Hdahmp)2]SO4, [Pd(Hdahmp)(dahmp)]Cl, [Pt(dahmp-H)]+n, [M(bpy)(dahmp]Cl, [M(bpy)(Hdahmp]Cl2 (M(II)=Pd, Pt), [Ru(dahmp)2(PPh3)2], [Rh(dahmp)2(H2O)2]Cl, [Ag2(Hdahmp)2], cis-[MoO2(dahmp∗3HCl)2] and cis-[MoO2(Hdahmp)(DMF)Cl]Cl have been synthesized and characterized on the basis of elemental analyses, IR, NMR (1H, 13C, 31P), UV–Vis and ESI-mass spectrometry, thermal and molar conductivity measurements. 5,6-Diamino-4-hydroxy-2-mercaptopyrimidine exhibits five different modes of chelation: (i) a neutral bidentate ligand through the cyclic nitrogen (N-3) and thione sulfur atoms, (ii) a mononegative bidentate ligand through the deprotonated cyclic nitrogen (N-1) and thione sulfur atoms, (iii) a mononegative bidentate ligand through the cyclic nitrogen (N-3) and deprotonated hydroxy centers, (iv) a tetradentate ligand through the cyclic nitrogens (deprotonated N-1, N-3), thione and deprotonated hydroxy oxygen centers, and (v) a mononegative bidentate through the deprotonated cyclic nitrogen (N-3) and ketonic oxygen atoms. The free Hdahmp and several of its complexes have been tested against the human serous ovarian cancer (OV-90) and human ovarian cancer (OVCAR-8) cell lines.