Synthesis, Spectral and DFT Characterization, PASS Predication, Antimicrobial, and ADMET Studies of Some Novel Mannopyranoside Esters

Abstract

Due to the biodegradability and drug-likeness properties sugar esters (SEs) are getting especial attention to the synthetic and bioorganic chemists. In this context, we have synthesized several 6-O-pentanoyl mannopyranoside esters (5-9) with alkanoyl and sylfonyl chains reasonably in good yields. Both the prediction of activity spectra for substances (PASS) and in vitro tests indicated that these mannopyranoside esters possess better potentiality against fungal pathogens than the bacterial organisms. These SEs were also optimized with quantum chemical density functional theory (DFT), and various thermodynamic properties like frontier molecular orbital, and molecular electrostatic potential (MEP) were calculated and discussed. Absorption, distribution, metabolism, excretion, and toxicity (ADMET) calculations indicated that these SEs can pass through blood brain barrier and less toxic. Drug-likeness results indicated good conditions for alkanoyl esters rather than sulfonyl esters despite their promising antifungal results. All the in vitro and in silico results indicated that the combination of pentanoyl (C5) and lauroyl (C12) chains in mannopyranoside framework, as in 9, might be a potential candidate for novel antifungal agent.

Keywords

• Methyl α-D-mannopyranoside, Selective acylation, Antimicrobial agents, DFT calculations, ADMET.