Document Type : Regular Article
Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, 4331, Bangladesh
Department of Chemical Engineering and Energy Sustainability, Faculty of Engineering, Universiti Malaysia Sarawak, Jalan Datuk Mohammad Musa, Kota Samarahan, 94300, Malaysia
Department of Chemistry, European University of Bangladesh, Gabtoli, Dhaka, 1216, Bangladesh
Extensive research in the past decades indicated that the sugar ester (SE) type biomolecules bring long-chain fatty acids with sugar moieties into the plant cells, and play various important roles in food, surfactants, innovative green materials, and biological properties. Thus, methyl α-D-glucopyranoside (4) upon dimolar isopentanoylation furnished the methyl 2,6-di-O-isopentanoyl-α-D-glucopyranoside (5) indicating selectivity at C-2 and C-6 positions. Compound 5 was further acylated and obtained 3,4-di-O-acyl esters 5-8 in good yields. In vitro antifungal activities of these compounds exhibited moderate to good zone of inhibition. To rationalize these results molecular docking studies of 4-8 are performed against lanosterol 14-α-demethylase (CYP 51). Attachment of acyl ester chain(s) in the glucopyranoside ring added more lipophilicity and affected their fungal inhibition via binding with lanosterol 14-α-demethylase enzyme. Especially, isopentanoyl group(s) with lauroyl group(s) as in 8 showed better binding affinity than that of fluconazole indicating the better efficiency of SEs.