Evaluation of antimicrobial, antiquorum sensing, and cytotoxic activities of new vanillin 1,2,3-triazole derivatives.

Vanillin (), the main constituent of vanilla species, was used as a starting natural scaffold for the synthesis of five new (-) and one known () triazole derivatives click chemistry using the copper (I)-catalyzed azide-alkyne cycloaddition method. Vanillin and its new derivatives; 4-{1-[2-Hydroxymethyl-5-(5 methyl-2,4-dioxo-3,4-dihydro-2-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-1[1,2,3]triazol-4-ylmethoxy}-3-methoxy-benzaldehyde (); [4-(4-Formyl-2methoxy-phenoxymethyl)-[1,2,3]triazol-1-yl]-acetic acid methyl ester (); 4-[1-(4-Acetyl-phenyl)-1-[1,2,3]triazol-4-ylmethoxy]-3-methoxy-benzaldehyde (); 4-[4-(1-Benzyl-1-[1,2,3]triazol-4-ylmethoxy)-3-methoxy-phenyl]-but-3-en-2-one (); and 4-[4-(1-Benzyl-1-[1,2,3]triazol-4-ylmethoxy)-3-methoxy-phenyl]-4-hydroxy-butan-2-one (), as well as the previously known derivative () were subjected to antimicrobial, antiquorum-sensing and cytotoxic evaluation. Compounds - possessed the most notable enhancement in the anti-bacterial activity against , and antifungal activity against . However, compounds and exhibited high antiquorum-sensing activity against using catechin as a positive control. Compounds - demonstrated selective cytotoxicity against MCF-7 and HepG2 cancer cells compared to normal lung fibroblast cells (WI-38). These findings proved the usefulness of synthesis bioactive derivatives from vanillin through chemical modifications.