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Synthesis, Pass Predication of Antimicrobial Activity and Pharmacokinetic Properties of Hexanoyl Galactopyranosides and Experimental Evaluation of their Action against Four Human Pathogenic Bacteria and Four Fungal Strains

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Pharmaceutical Chemistry Journal Aims and scope

Direct unimolar hexanoylation of methyl α-D-galactopyranoside (MDG) at low temperature gave 6-O-hexanoate in 53% yield indicating regioselectivity at the C-6 position. To develop galctopyranoside-based potential antimicrobial sugar esters (SEs), 6-O-hexanoate was further converted into seven new 2,3,4-tri-O-acyl esters in reasonably good yields. Prediction of Activity Spectra for Substances (PASS) and in vitro antimicrobial studies established these SEs as better antifungal agents as compared to antibacterials. ADMET properties reveal that these SEs can penetrate through the blood-brain barrier, they are P-glycoprotein inhibitors, noncarcinogenic, and possess lower median lethal dose (LD50) values. Drug likeliness calculations indicate that these MDG esters are in good agreement with several important parameters. Structure-activity relationship (SAR) of these SEs indicated that the incorporation of hexanoyl and octanoyl group(s) increased the antimicrobial potential of MDG.

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Acknowledgments

The authors would like to thank Ministry of Science and Technology, Bangladesh for financial support (Sl. No. 529, Physical Science, 2018 – 2019) in completing this work.

Conflict of Interest

The authors declare that they have no conflicts of interest.

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Authors and Affiliations

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

    Mohammed M. Matin, Md. Mosharef H. Bhuiyan, Sayed M. Kibria & Md. S. Hasan

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  1. Mohammed M. Matin
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  2. Md. Mosharef H. Bhuiyan
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Correspondence to Mohammed M. Matin.

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Matin, M.M., Bhuiyan, M.M.H., Kibria, S.M. et al. Synthesis, Pass Predication of Antimicrobial Activity and Pharmacokinetic Properties of Hexanoyl Galactopyranosides and Experimental Evaluation of their Action against Four Human Pathogenic Bacteria and Four Fungal Strains. Pharm Chem J 56, 627–637 (2022). https://doi.org/10.1007/s11094-022-02687-y

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