Synthesis of Some Novel Nanosized Chelates of Anchoring Bisazo Dye 5-[5-(4,6-Dioxo-2-thioxo-hexahydro-pyrimidin-5-ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione and Their Applications as Antioxidant and Antitumor Agents

Abstract

A novel bisazo 5-[5-(4,6-dioxo-2-thioxo-hexahydro-pyrimidin-5ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione (H 4 L) ligand has been synthesized from diazotization coupling between naphthalene-1,5diamine and 2-thiobarbituric acid. Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Fe(III) chelates were prepared. All prepared compounds were characterized by different techniques. The azo groups did not participate in chelation according to the infrared spectra, whereas the thioamide group did participate. The azo dye ligand coordinated with all metallic ions in a neutral−keto−thiol structure and behaved as a bi-and tridentate moiety. Zinc, manganese, and iron chelates had an octahedral structure, while nickel and cobalt chelates had a tetrahedral structure, but the copper chelate had a square pyramidal geometry. The thermal behavior of all prepared compounds was investigated and thermokinetic parameters were also discussed. X-ray diffraction (XRD) data reflected that Fe(III) and Zn(II) complexes were crystalline while the Cu(II) complex was amorphous. Calcination of the Fe(III) complex at 600 °C yielded a nanosized Fe 2 O 3 crystalline phase, elucidated by XRD and transmission electron microscope. The novel azo dye and some of its chelates were tested against HepG-2. The Fe 2 O 3 nanooxide showed remarkable activity against the HepG-2 cell line rather than its precursor Fe(III) complex. Co(II) had a higher antioxidant activity than the other investigated complexes. In both activities, the Cu(II) complex did not show any activity. Molecular modeling and some theoretical studies were validated, and the experimental results were interpreted.

Synthesis, characterization, thermal, anticancer studies, and density functional theory for potentially active pyrimidine‐based complexes

“…The activity was higher for Co(II) and Zn(II) complexes than other compounds. The antioxidant and antitumor activities of our 5‐((2‐hydroxy‐4,6‐dioxo‐1,4,5,6‐tetrahydropyrimidin‐5‐yl)diazenyl)naphthalen‐1‐yl)diazenyl) pyrimidine 2,4,6 (1H,3H,5H)‐trione and its chelates are higher than that of 5‐[5‐(4,6‐dioxo‐2‐thioxo‐hexahydro‐pyrimidin‐5‐ylazo)‐naphthalen‐1‐ylazo]‐2‐mercapto‐1H‐pyrimidine‐4,6‐dione analogue and its chelates that were published by our group 44 . IC 50 of Cu complex of 5‐[5‐(4,6‐dioxo‐2‐thioxo‐hexahydro‐pyrimidin‐5‐ylazo)‐naphthalen‐1‐ylazo]‐2‐mercapto‐1H‐pyrimidine‐4,6‐dione was 57.5 μg/mL that decreased to 23 μg/mL for the prepared Cu chelate of 5‐((2‐hydroxy‐4,6‐dioxo‐1,4,5,6‐tetrahydropyrimidin‐5‐yl)diazenyl)naphthalen‐1‐yl)diazenyl) pyrimidine 2,4,6 (1H,3H,5H)‐trione in the current study, also in comparison between Zn(II) chelates of the two ligands, IC50 decreased from 18.7 to 13 μg/mL.…”

“…The ligand exhibited an oxidizing impact that is evidenced by the final metal oxide residue 44 . In addition, the complexes had greater thermal stability than the uncoordinated ligand, as a result of the chelate's structure.…”

“…The ligand exhibited an oxidizing impact that is evidenced by the final metal oxide residue. 44 In addition, the complexes had greater thermal stability than the uncoordinated ligand, as a result of the chelate's structure. [Sm 3 (H 4 L)(OH) 7 (NO 3 ) 2 .H 2 O].4.5EtOH had the highest thermal stability, which may be owing to the large number of solvent molecules involving hydrogen bond formation.…”

“…The antioxidant and antitumor activities of our 5-((2-hydroxy-4,6-dioxo-1,4,5,6-tetrahydropyrimidin-5-yl)diazenyl)naphthalen-1-yl)diazenyl) pyrimidine 2,4,6 (1H,3H,5H)-trione and its chelates are higher than that of 5-[5-(4,6-dioxo-2-thioxohexahydro-pyrimidin-5-ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione analogue and its chelates that were published by our group. 44…”

Synthesis, Characterization, Antimicrobial, Density Functional Theory, and Molecular Docking Studies of Novel Mn(II), Fe(III), and Cr(III) Complexes Incorporating 4-(2-Hydroxyphenyl azo)-1-naphthol (Az)

“…Over the course of the past four decades, azo dyes that include heterocyclic rings have made substantial contributions to the field of coordination chemistry . Research in the fields of biology, electrochemistry, and analysis may all make use of these substances in a variety of different ways .…”