Co (II), Ni (II), and Cu (II) complexes of 4,6‐bis(2‐hydroxynaphthalen‐1‐yl)methyl‐ene)hydrazono)ethyl)benzene‐1,3‐diol: Synthesis, spectroscopic, biological, and theoretical studies

• Published in: Applied organometallic chemistry Vol. 36; no. 5
• Main Authors: Samy, Fatma, Shebl, Magdy
• Format: Journal Article
• Language: English
• Published: Chichester Wiley Subscription Services, Inc 01.05.2022
• Subjects: 4,6‐diacetylresorcionl; Anticancer properties; antitumor and antimicrobial activity; Benzene; Binding; Chemical synthesis; Chemistry; Coordination compounds; Copper; DNA binding and molecular docking; Electron paramagnetic resonance; Electron spin; Gravimetric analysis; Hydrazones; Hydrocarbons; Infrared analysis; Magnetic moments; Magnetic permeability; Molecular docking; Nickel; NMR; Nuclear magnetic resonance; Spin resonance; theoretical study; Thermal analysis; Unit cell; X-ray diffraction
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.6650

A new hydrazone ligand 4,6‐bis(2‐hydroxynaphthalen‐1‐yl)methyl‐ene)hydrazono)ethyl)benzene‐1,3‐diol (H4L; DHNAPH) was synthesized by the reaction of 4,6‐bis(1‐hydrazonoethyl)benzene‐1,3‐diol (NH2DAR) with 2‐hydroxy 1‐naphthaldehyde. Co (II), Ni (II), and Cu (II) complexes ([M2L(H2O)6].nH2O.mEtOH (M = Co, Ni or Cu; n = 0.5 or 1; and m = 0.5 or 0) of DHNAPH have been successfully synthesized. Characterization of DHNAPH and its complexes was performed by analytical, spectral (infrared [IR], mass, UV–Vis, 1H NMR, and electron spin resonance [ESR]), powder X‐ray diffraction (XRD), magnetic susceptibility, molar conductivity, and thermal gravimetric analysis (TGA) techniques. The analytical data, magnetic moments, and spectral studies recognized octahedral geometries for DHNAPH complexes. DHNAPH acts as a bis (dibasic tridentate) via (C=N azomethine and 2 OH) with metal in complexes. The XRD patterns for DHNAPH and its complexes indicate crystalline nature of DHNAPH and its Cu complex. DHNAPH has triclinic system, while copper‐DHNAPH has a tetragonal system with different unit cell parameters. Theoretical studies showed that there is a good relation between experimental IR data and theoretical calculation. The activity of DHNAPH and its complexes against Hepatocellular carcinoma, fungi, and bacteria has been tested. The new complexes are more active than DHNAPH, and the highest antitumor activity was given by copper (II) complex, which showed lower IC50 than that of Cisplatin. The DNA binding of DHNAPH and Cu‐DHNAPH has been investigated. Molecular docking studies showed that all the tested compounds show good binding scores revealing good fitting in between the DNA strands. There is an agreement between docking data and DNA binding results. New binuclear complexes have been synthesized and characterized by analytical, spectral (infrared [IR], mass, UV–Vis, and electron spin resonance [ESR]), magnetic susceptibility, molar conductivity measurements, scanning electron microscope (SEM), X‐ray diffraction (XRD), and thermal gravimetric analysis (TGA) techniques. There is good correlation between theoretical parameters and the experimental data. The activity of DHNAPH‐compounds against HepG‐2, fungi, and bacteria has been tested. The docking data agree with DNA binding results. The copper (II) complex has the highest antitumor activity.