Synthesis, characterization and antibacterial properties of some halogenated glucose derivatives

Abstract

We synthesised a series of glucose derivatives containing different halogens and studied their biological activity on two species of pathogenic bacteria. The synthesis requires multiple steps, starting with methyl-α-D-glucopyranoside, which reacts with benzaldehyde dimethyl acetal to protect the hydroxyls at 4- and 6-carbons to obtain compound 2. We treated compound 2 with bis(2-chloroethyl) ether under the Williamson etherification condition, in the presence of phase transfer catalysts, to produce compound 3. We treated compound 3 with sodium iodide under Flenksteien reaction conditions to obtain derivative 4. We characterized all compounds using spectroscopic instruments. Finally, we studied the antibacterial activity against Staphylococcus aureus and Escherichia coli. It is evident that the chlorine and iodine atoms significantly contribute to the antibacterial activity against the bacteria. After penetration, the sugar derivatives inside the bacterial cells degrade, releasing free chlorine or iodine ions that kill the bacteria.