Ligational behavior of a new bis (bidentate NO) donor hydrazone towards Co (II), Ni (II), and Cu (II) ions: Preparation, spectral, thermal, biological, docking, and theoretical studies

Abstract

Reaction of 4,6‐bis(1‐hydrazonoethyl)benzene‐1,3‐diol with 3‐nitrobenzaldehyde gave the new bis (bidentate) hydrazone ligand; 4,6‐bis(3‐nitrobenzalen‐1‐yl)methylene)hydrazono)ethyl)benzene‐1,3‐diol (H2L; H2BisBD). Binuclear Co (II), Ni (II), and Cu (II) complexes of general formula ([M2BisBD(H2O)x (EtOH)y].nH2O; M = Co, Ni or Cu, x = 4 or 6, y = 2 or 0; n = 1 or 0) have been successfully prepared. The structures of H2BisBD and its complexes have been characterized by means of analytical, spectroscopic (infrared, proton nuclear magnetic resonance, mass, UV–Vis, and electron spin resonance), molar conductivity, and magnetic susceptibility measurements and thermal gravimetric analysis. Octahedral geometrical structures were proposed for all complexes in which the hydrazone ligand behaves as a bis (monoanionic bidentate) via azomethine nitrogen and phenolic oxygen donor atoms. The scanning electron microscopy refers that the copper (II) complex is in the nano scale. The ligand and its complexes showed antitumor activity against Hepatocellular carcinoma. Complexation process improved the antitumor activity, and copper (II) complex showed a promising activity, which agree with docking data. Theoretical studies for the prepared compounds were calculated using Hyperchem program at PM3.

Structural variety of Cu (II), Ni (II), and Co (II) complexes of a hydrazone based on 5‐acetyl‐4‐hydroxy‐2H‐1,3‐thiazine‐2,6(3H)‐dione: Synthesis, spectroscopic, density functional theory, antitumor, and docking studies

“…This order is observed in the previously published hydrazone complexes. [94,95] It's possible that copper's significant function in a number of enzymes that catalyze a variety of processes is what accounts for the copper (II) complex's higher activity. [96,97] Within copper (II) complexes, the order of activity is bromo > sulphato > acetato > nitrato-complexes showing that the antitumor activity of the current complexes is influenced by the type of anion.…”

Complexation behavior of copper and zinc divalent ions towards diisatin malonyl dihydrazone ligand with biological and catalytic assessments

“…18 Samy and Shebl studied the bio-action of N,O-bidentate hydrazone chelates (with divalent Cu 2+ , Co 2+ , and Ni 2+ ions) as antitumor drug candidates, experimentally and through docking examination against hepatocellular carcinoma. 19 The chemotherapeutic features of Schiff base hydrazone complexes of Pd 2+ , Cu 2+ , and Cd 2+ ions were an urgent issue, which assigned recently to report their biological screening. 20 Other related published works of Co 2+ and Cu 2+ hydrazone complexes have been employed for the therapeutic treatments of COVID-19.…”

Bimetallic bis-Aroyldihydrazone-Isatin Complexes of High O=V(IV) and Low Cu(II) Valent Ions as Effective Biological Reagents for Antimicrobial and Anticancer Assays

“…Currently, many organic derivatives of copper (II) hydrazone-based organometallic reagents have been synthesized for many biological studies, such as Cu 2+ , Ni 2+, and Fe 3+ complexes derived from the dioxanylidene hydrazinyl benzoic acid ligand, as highly reactive antimicrobial reagents [ 18 ]. Furthermore, Samy and Shebl reported the antitumor activity of newly designed N , O -hetero pincer chelating hydrazone complexes of copper(II), nickel(II), and cobalt(II) ions within docking studies against hepatocellular carcinoma [ 19 ]. Additionally, new chemotherapeutic metallo-organic chelates have been designed, such as the new Schiff base hydrazone complexes of Pd 2+ , Cu 2+, and Cd 2+ ions [ 20 ] and of Co 2+ and Cu 2+ ions [ 21 ], and have been biologically screened as treatments for COVID-19.…”

“…VOLph exhibited base peaks at 783.07 and 782.59 for the mass portion for [ML + 1] (C34H30N6O10V2), i.e., the positive mode, and also at 683.31 (C29H21N6O8V2), 584.03 (C24H14N6O6V2), 532.27 (C20H10N6O6V2), 482.23 (C16H8N6O6V2), 434.32 (C12H7N6O6V2), 402.08 (C12H6N4O6V2), 243.20 (C9H6N2O3V), and 164.18 m/z (C3H2N2O3V) for the residual mass portion fragmentation of VOLph (FigureS6). The EI-Mass spectra for CuLph were reported firstly with a remarkable base peak at 578 19. and 577.23 m/z for [ML − 2Cl − ] (C24H14Cu2N6O4), and at 525.33 (C20H10Cu2N6O4), 473.04 (C16H8Cu2N6O4), 450.86 (C14H7Cu2N6O4), 425.00 (C12H6Cu2N6O4), 395.36 (C12H5Cu2N4O4),…”