Spectroscopic and computational study of chromone derivatives with antitumor activity: detailed DFT, QTAIM and docking investigations

Abstract

Theoretical investigations of three pharmaceutically active chromone derivatives, (E)-3-((2,3,5,6-tetrafluorophenyl)hydrazono)methyl)-4H-chromen-4-one (TPC), (E)-3-((2-(2,4,6-trifluorophenyl)hydrazono)methyl)-4H-chromen-4-one (FHM) and(E)-3-((2-(perfluorophenyl)hydrazono)methyl)-4H-chromen-4-one (PFH) are reported. Molecular geometries, vibrational spectra, electronic properties and molecular electrostatic potential were investigated using density functional theory. Quantum theory of atoms in molecules (QTAIM) study shows that the maximum of ellipticity parameters in the existing bonds in TPC, FHM and PFH, attributes to the bonds involving in aromatic region points toward the π-bond interactions in the molecules. Based on energy gap (1.870, 1.649 and 1.590 eV) and electrophilicity index (20.233, 22.581 and 23.203 eV) values of TPC, FHM and PFH, we can conclude that all molecules have more biological activity. The molecular electrostatic potential maps were calculated to provide information on the chemical reactivity of the molecule and also to describe the intermolecular interactions. All these studies including docking studies, help a lot in determining the biological activities of chromone derivatives. Activities of chromone derivatives are compared with 5-fluorouracil and azathioprine (antitumor, antiproliferative standards) and were found to be higher than reference ones.

Volumetric, Compressibility, Spectroscopic, and Theoretical Evaluation of Interactions between Caffeine and Ethanolammonium Butyrate in Aqueous Solutions

“…Density functional theory (DFT) calculations have been performed using the Gaussian computational package to investigate the interionic interaction between [EABu] and CAF. CAM-B3LYP exchange–correlation function in conjunction with the 6-311G ++ (2d, 2p) basis set was employed to perform the geometry optimizations in this work on the Gaussian 09 computational package. − Vibrational frequencies of optimized structures were calculated and all the real values of frequency confirm that the optimized geometry corresponds to true minima. The binding energies for isolated ionic liquid were corrected with the basis set superposition error (BSSE) using the Boys Bernardi counterpoise technique .…”

Theoretical Study of 2-(Trifluoromethyl)phenothiazine Derivatives with Two Hydroxyl Groups in the Side Chain-DFT and QTAIM Computations

“…On the other hand, the quantum theory of atoms in molecules (QTAIM) describes atomic and bond properties based on molecular electron-density distributions [ 3 ]. Both DFT and QTAIM have been used in theoretical investigations on different compounds with anticancer activity [ 4 , 5 , 6 ]. Using these theories, the activity of the chemical compounds may be explained in terms of the predicted chemical reactivity descriptors as well as molecular electrostatic potential.…”

“…DFT and the molecular docking studies of Al Sheikh Ali et al [ 4 ] confirmed the results of in vitro experiments on anticancer activity of triazoles derivatives against Caco-2, HCT116, HeLa, and MCF7 cell, indicating the most active among studied compounds. Mary et al [ 5 ] used DFT theory to investigate the molecular geometries, vibrational spectra, electronic properties, and molecular electrostatic potential of pharmaceutically active chromone derivatives. The results of these calculations, together with the QTAIM studies, allowed for the conclusion that the studied compounds possess higher anticancer activity as compared with antitumor standards (5-fuorouracil and azathioprine).…”