Synthesis, Antifungal Activity, and Molecular Docking Studies of Some New Di-O-Isopentanoyl Glucopyranosides

Document Type : Regular Article

Authors

1 Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, 4331, Bangladesh

2 Department of Chemical Engineering and Energy Sustainability, Faculty of Engineering, Universiti Malaysia Sarawak, Jalan Datuk Mohammad Musa, Kota Samarahan, 94300, Malaysia

3 Department of Chemistry, European University of Bangladesh, Gabtoli, Dhaka, 1216, Bangladesh

10.22036/pcr.2022.334577.2057

Abstract

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.

Graphical Abstract

Synthesis, Antifungal Activity, and Molecular Docking Studies of Some New Di-O-Isopentanoyl Glucopyranosides

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History

  • Receive Date: 17 March 2022
  • Revise Date: 05 May 2022
  • Accept Date: 23 May 2022

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