Synthesis and characterization studies of 3‐formyl chromone Schiff base complexes and their application as antitumor, antioxidant and antimicrobial

Abstract

A novel Schiff base namely (E)‐3‐((2,6‐dihydroxypyrimidin‐4‐ylimino)methyl)‐4H‐chromen‐4‐one and its Co (II), N (II)i, Cu (II) and Cd (II) complexes have been synthesized and proved by elemental analysis, molar conductance, thermal analysis (TGA), Inductive Coupled plasma (ICP), magnetic moment measurements, X‐ray powder diffraction, IR, EI‐mass,1H NMR, 13C NMR,UV–Vis. and ESR spectral studies. On the basis of these data, it is evident that the Schiff base acts as bidentate via oxygen atom of carbonyl group and azomethine nitrogen atom for Co (II) complex; monobasic bidentate ligand for Ni (II), Cu (II) and Cd (II) complexes via oxygen atom of hydroxyl group and nitrogen atom of pyrimidine ring. The results showed all complexes have octahedral geometry. The average particle size of the ligand and its complexes were found to be 1.010–0.343 nm. The pharmacological action (antioxidant, antimicrobial and anticancer) of the prepared compounds is studied. The antitumor activity of the ligand and its metal complexes is evaluated against human liver carcinoma (HEPG2) cell. The data displayed the Co (II) complexes strong cytotoxicity where IC50 values of Co (II) complex and 5‐fluorouracil (stander drug) are 9.33 and 7.86 μg/ml respectively. The Co (II) and Cd (II) complexes have antibacterial activity more than ampicillin (stander drug). The interaction of the synthesized compounds with calf‐thymus DNA (CT‐DNA) has been performed via absorption spectra and viscosity technique. The DNA‐ binding constants have been determined.

New nickel (II), cobalt (III), and iron (III) complexes with N′‐[(2‐aminochromon‐3‐yl)methylidene]benzohydrazide: Synthesis, characterization, solvatochromic shift, dipole moment, and DFT calculations

“…The emission spectral data of the free ligand, HL, and its metal complexes (1)(2)(3) in solid state at room temperature and their 1 Â 10 À4 M DMF solutions are collected in Table 6. The data in Table 6 indicate improvement of fluorescence intenstity of all complexes compared with the free ligand.…”

“…Chromones are naturally occurring compounds and possess a wide range of biological activities such as antimicrobial [1] anti-inflammatory, [2] antioxidant, [3] antitumor, [4] antiproliferative, [5] anti-HIV, [6] and antimalarial activities. [7] Metal complexes containing chromones are widely examined because of their wide use in biological field.…”

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

“…There is a continuous interest in synthesis of chromones and chromone‐based ligands and their complexes because of variable applications of these compounds, namely, antimicrobial, [ 9 ] antitumor, [ 10 ] antiplasmodial and anti‐inflammatory, [ 11 ] antioxidant, [ 12 ] and anti‐Alzheimer [ 13 ] properties as well as other biological and pharmaceutical applications. [ 14 ]…”

Schiff Base Ligand 3-(-(2-Hydroxyphenylimino) Methyl)-4H-Chromen-4-One as Colorimetric Sensor for Detection of Cu2+, Fe3+, and V5+ in Aqueous Solutions

“…Schif bases derived from 3-formyl chromone have been studied signifcantly and have attracted the attention of chemists and researchers as they can easily bind with metal ions, forming metal complexes that have many applications [15,16]. Chromone-based azomethine colorimetric chemosensors were reported by Rezaeian et al and successfully used to detect and recognize Cu 2+ , Zn 2+ , and CN − ions [17].…”