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

Abstract

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.

Zn(II), Mn(III), and Co(III) complexes of Schiff base derived from 2‐hydroxy‐1‐naphthaldehyde: Synthesis, spectral surveys, single crystal structure studies, Hirshfeld surface analysis, density functional theory calculation, molecular electrostatic potential, and molecular docking evaluations

“…[30][31][32] Structural changes such as changing the type of central metal and replacing different ligands have been used in different ways that develop and facilitate different properties and applications of Schiff bases. [33][34][35][36] Schiff base compounds derived from naphthaldehyde have attracted the attention of chemists due to their reactivity in various chemical reactions, structural flexibility, coordination with metal ions, inherent stability, optical properties, and so on. 1,37 Also, Schiff base derivatives of naphthaldehyde have potential biological and medicinal activity.…”

“…Therefore, extensive studies have been conducted in this field using various Schiff base metal complexes as corrosion inhibitors 26–29 ; inhibitor molecular shape, concentration, and metal type are considered effective factors in corrosion inhibitors 30–32 . Structural changes such as changing the type of central metal and replacing different ligands have been used in different ways that develop and facilitate different properties and applications of Schiff bases 33–36 . Schiff base compounds derived from naphthaldehyde have attracted the attention of chemists due to their reactivity in various chemical reactions, structural flexibility, coordination with metal ions, inherent stability, optical properties, and so on 1,37 .…”

“…Biological activity and molecular docking studies of the complexes were studied. The results showed that new complexes can be proposed for potential biological activity 34 . By these facts showing the importance and significant applications of the Schiff compounds, the authors became interested in preparing Schiff base ligands ( HL ) by condensation 2‐hydroxy‐1‐naphthaldehyde with 2‐methoxyethylamine and then a new series of Zn(II), Mn(III), and Co(III) complexes (Scheme 1).…”

N′-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling

“…As well, the benzohydrazide derivatives and its metal complexes have been employed in many biological applications, as anti-inflammatory, antibacterial, and anticancer agents. The significant biological activity and extensive range of uses of benzohydrazide may be attributed to the presence of its potential keto-enol tautomeric forms, which arise from the electron delocalization between the adjacent amine and carbonyl groups [ 8 , 19 – 22 ].…”

Synthesis, characterization, DFT calculations and biological activity of new Schiff base complexes

“…The acylhydrazone cyclic compounds are a significant class of heterocyclic chemicals with a variety of biological effects [ [4] , [5] , [6] ]. The simplicity of synthesis makes it possible to build a variety of chemical libraries for the search for potential bioactive compounds.…”