DFT Based Pharmacokinetic, Molecular Docking, and ADMET Studies of Some Glucopyranoside Esters

Abstract

Monosaccharide esters (MEs) are getting more attention from bioorganic chemists due to their biodegradable and drug-likeness properties. As a consequence, carbohydrate derivatives (sugar-based esters, SEs) are an essential part of medicinal chemistry. In this context, density functional theory (DFT) with B3LYP/ 3-21G has been employed to optimize the methyl 4,6-O-benzylidene-α-D-glucopyranoside (3) of methyl α-D-glucopyranoside (2) and its protected acyl esters 4-6. The prediction of activity spectra for substances (PASS) of these compounds showed better antifungal functionalities than the antibacterial potentiality. Thermodynamic properties and molecular electrostatic potential (MEP) of these MEs indicated their stability and both the electrophilic and nucleophilic attack sites. Due to their better antifungal potentiality, molecular docking was conducted against fungal protein lanosterol 14α-demethylase (3JUS), and SARS-CoV-2 main protease (6LU7) along with absorption, distribution, metabolism, excretion, and toxicity (ADMET) studies. The study indicated a better binding affinity of some esters compared to the standard antifungal and COVID-19 related drug hydroxychloroquine (HCQ).