Coordinating behavior of hydrazone ligand bearing chromone moiety towards Cu(II) ions: Synthesis, spectral, density functional theory (DFT) calculations, antitumor, and docking studies

Abstract

A new hydrazone ligand (FCSH; HL) was successfully synthesized by the reaction of salicylaldehyde hydrazone with 3‐formylchromone. Seven copper(II) hydrazone complexes have been synthesized by using several copper(II) salts (acetate, nitrate, sulfate, perchlorate, chloride, and bromide). Elemental analysis, electronic, infrared, mass, nuclear magnetic resonance, electron spin resonance spectra, thermal analysis, molar conductivity, and magnetic susceptibility measurements were used to characterize structures of the hydrazone ligand and its complexes. The ligand behaves as monobasic tridentate for all complexes except complex 2 (monobasic tetradentate) and complex 4 (neutral tridentate). All metal complexes exhibited octahedral geometries. With the aid of Coats–Redfern equations, the kinetic parameters (Ea, A, ∆H, ∆S, and ∆G) of the thermal decomposition stages were calculated and discussed. At the B3LYP/6‐311G(d,p) level engaged in the Gaussian 09 program, density functional theory (DFT) calculations were carried out to inspect the optimized structures of the chelating agent and its complexes. The hydrazone ligand and its copper(II) complexes showed antitumor activity towards HepG2 cell line. The docking study of the hydrazone ligand and its copper(II) complexes was investigated with the active site of the CDK2 kinase.

Co(ii), Ni(ii), Cu(ii) and Cd(ii)-thiocarbonohydrazone complexes: spectroscopic, DFT, thermal, and electrical conductivity studies

“… 82,83 The magnetic moment of the Cu( ii ) complex appeared at 1.8 B.M., which agrees with the value of the octahedral geometry. 84,85 …”

“…82,83 The magnetic moment of the Cu(II) complex appeared at 1.8 B.M., which agrees with the value of the octahedral geometry. 84,85 The yellow Cd(II) complex displayed absorption bands at 288, 318, and 415 nm that could be due to p-p*, n-p*, and CT transitions, respectively. The electronic spectrum of the Cd(II) complex does not include any specic evidence for stereochemistry, but octahedral geometry is proposed for the Cd(II) complex based on analytical, thermal, and infrared spectral evidence.…”

Synthesis, characterization, antibacterial, anticancer, and density‐functional theory studies of nano‐metal (II) oxime complexes

“…The 1 H NMR spectrum of [Pt( κ 2 ‐Saly) 2 ] complex (Figure 1b) showed similar signals to that of [Pd( κ 2 ‐Saly) 2 ], which can be described as follows: C H ═N and C═N–O H appeared as singlet beaks at δ 10.56 and 8.49 ppm, [ 34,35 ] while protons of phenyl ring appeared for separated peaks which are listed in the experimental part.…”

“…The 1 H NMR spectrum of [Pd( κ 2 ‐Saly) 2 ] complex (Figure 1a) showed the protons of C H ‐N and O H groups as singlets peaks at δ8.49 ppm and δ10.56 ppm, respectively. [ 34,35 ] The H 4 and H 1 displayed as doublet at 7.46 and 7.15 ppm with coupling constant of neighboring protons equal 7.80 Hz. Also, the spectrum displayed two triplet peaks at 7.30 ppm ( 3 J H‐H = 7.90 Hz) and 6.32 ppm ( 3 J H‐H = 7.90 Hz) due to the H 3 and H 2, respectively.…”

A binuclear copper(II) complex based on hydrazone ligand: Characterization, molecular docking, and theoretical and antimicrobial investigation

“…[97] These results indicate that the complexation of copper(II) to hydrazone ligands is an effective strategy to improve the biological properties of the free ligand, as reported previously for similar compounds. [23,27,[98][99][100]…”