Synthesis, PASS, In Silico ADMET and Thermodynamic Studies of Some Galactopyranoside Esters

Due to their biodegradability and lower sideeffects, many sugar esters (SEs) have received much attention from researchers and been widely applied in medicinal chemistry. In this respect, methyl 6-O-pentanoyl-α-d-galactopyranoside, obtained from methyl α-dgalactopyranoside (MDG) using direct site-selective unimolar pentanoylation, was converted into four 2,3,4-tri-O-acyl esters in reasonably high yields. All the compounds were characterized by spectroscopic techniques. The results of Prediction of Activity Spectra for Substances (PASS) analysis indicated that the MDG esters had many potential biological activities. More specifically, the alkyl ester derivatives had higher antimicrobial potential than those of the sulfonyl ester. In addition, their absorption, distribution, metabolism, excretion and toxicity (ADMET) prediction revealed that most of the SEs had acceptable drug-related safety parameters. In this regard, the thermodynamic properties of galactopyranosides were also investigated and are reported herein.