(E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)prop–2-en-1-one: DFT/TD-DFT-based investigations with distinct solvents and in silico ADME profiling

Abstract

The chalcone scaffold has become one of the privileged structures frequently encountered in medicinal chemistry for the discovery of new and effective drug candidates. In recent years, chalcone derivatives have attracted intense attention from both experimental and theoretical researchers due to their ease of synthesis and wide range of biological activities. Herein, quantum chemical-based calculations were performed on chalcone derivative (E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)prop–2-en-1-one. Density functional theory (DFT) method was applied with the B3LYP hybrid functional and 6-311++G (d, p) basis set. The structural, electronic, energetic and reactivity properties of the mentioned chalcone derivative were examined. Bond parameters and vibrational analysis results were compatible with experimental data. The energy gap (∆E) values corresponding to acetonitrile, DMSO and water phases were calculated as 3.753, 3.750 and 3.747 eV, respectively. Also, the reactive regions of the molecule were visualized with molecular electrostatic potential (MEP) maps. The excited state characteristics of the title compound in water, acetonitrile and DMSO environments were calculated by the TD-DFT method. All absorption wavelengths could be qualified as π→π* and n→π* transition type. A bioavailability radar was created by calculating some physicochemical parameters such as lipophilicity, TPSA, and water solubility. ADME properties were predicted from pharmacokinetics and drug likeness data.