In this work we present our efforts towards the synthesis of S-glycosyl quinolones with potential antimicrobial activity. The synthesis of the quinolone core was achieved starting from the aniline, which was submitted to coupling with Meldrum acid and subsequent cyclization with Eaton's reagent. The heterocycle was further dibenzylated to functionalize C-3, and glycosylated under palladium catalysis with XantPhos as ligand. With this methodology a set of glycosylated quinolones was obtained; the latter were evaluated as antimicrobial agents. The preliminary results showed that the presence of an hydroxyl group at C-4 and a deprotected glycosyl moiety are crucial to mantain the bioactivity. The reactivity at C-6 and C-8 of the quinolone in the glycosylation step, the possibility of glycosylation with a bromine substituent in the aromatic ring and the use of 1,2-trans monosaccharides (i.e. mannose) will be discussed. In order to expand the possible applications of this class of molecules, we also present an additional docking study aimed to find a promising candidate for cytotoxicity studies.

Synthesis of 6-S-glycosyl-3,3-dibenzyl-4-hydroxy-quinolon-2-ones as antimicrobial and cytotoxic agents using a catalytic palladium cross-coupling strategy

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