Synthesis, characterization, computational and biological activity of novel hydrazone complexes

Abstract

In this work, novel hydrazone ligands were prepared by the reaction of chloroanthranilic acid diazonium salt with acetylacetone (L 1 ), ethyl acetoacetate (L 2 ) and diethyl malonate (L 3 ). The prepared compounds were reacted with some transition metals like Ni(II), Cu(II), and Fe(III). The structures of the prepared complexes were confirmed using nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR), distortionless enhancement by polarization transfer (DEPT), heteronuclear single quantum coherence (HSQC-NMR), correlated spectroscopy (COSY-NMR), Fouriertransform infrared spectroscopy (FT-IR) and electrospray ionization mass spectrometry (ESI-MS). Also, the magnetic properties for the prepared complexes were studied using Gouy's method of susceptibility measurement. Also, there in silico docking and in vitro antibacterial activities were investigated and the results showed that Ni complexes have the highest antimicrobial activity. The expected structures and conformers for the prepared ligands and complexes were examined and fully optimized using the level B3LYP/6-31G*.

Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

“…The N‐H proton of the indole ring exhibits a signal in the region of δ 11.78–11.95 ppm, remaining unaffected by complexation, suggesting that it does not coordinate with the tin atom. The resonance frequencies of the methylene protons and aromatic protons in the ligands lie within the range of δ 6.16–6.21 ppm and δ 6.52–8.62 ppm, respectively, and these resonances remain unaltered in the diorganotin (IV) complexes 60 . The aliphatic protons of ligand (4) resonate at δ 3.35–3.93 ppm.…”

“…The electronic spectra of both hydrazone ligands and their corresponding metal complexes were recorded in tetrahydrofuran (THF) as the solvent. The spectra of ligands showed two bands at 348–370 and 256–266 nm due to π‐π* and n‐π* transitions, respectively 60 . Upon complexation, these bands shifted to a higher frequency showing bathochromic shift.…”

“…The spectra of ligands showed two bands at 348-370 and 256-266 nm due to π-π* and n-π* transitions, respectively. 60 Upon complexation, these bands shifted to a higher frequency showing bathochromic shift. It has been reported that the metals are capable of forming dп-pп* bonds with ligands containing nitrogen and oxygen as the donor atoms.…”

“…The resonance frequencies of the methylene protons and aromatic protons in the ligands lie within the range of δ 6.16-6.21 ppm and δ 6.52-8.62 ppm, respectively, and these resonances remain unaltered in the diorganotin (IV) complexes. 60 The aliphatic protons of ligand (4) resonate at δ 3.35-3.93 ppm. Additionally, the emergence of new signals in the range of δ 0.60-1.58 ppm, corresponding to methyl, ethyl, butyl groups, and at δ 7.30-7.86 ppm, associated with phenyl groups directly linked to the central atom, suggests the formation of tin metal complexes.…”

Mixed isatin with 3-(2-(aryl)hydrazono)acetylacetone Mn(II), Co(II) and Ni(II) complexes: antibacterial evaluation and molecular properties prediction

“…Nintedanib (F) acts as triple angiokinase inhibitor [9] (Figure 1). In addition, arylhydrazono-1,3-diketone derivatives are useful synthons in the synthesis of a large number of biologically compounds [10][11][12].…”