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Vanillin ( 1 ), the main constituent of vanilla species, was used as a starting natural scaffold for the synthesis of five new ( 2 – 6 ) and one known ( 7 ) triazole derivatives  via  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 H -pyrimidin-1-yl)-tetrahydro-furan-3-yl]-1 H [1,2,3]triazol-4-ylmethoxy}-3-methoxy-benzaldehyde ( 2 ); [4-(4-Formyl-2methoxy-phenoxymethyl)-[1,2,3]triazol-1-yl]-acetic acid methyl ester ( 3 ); 4-[1-(4-Acetyl-phenyl)-1 H -[1,2,3]triazol-4-ylmethoxy]-3-methoxy-benzaldehyde ( 4 ); 4-[4-(1-Benzyl-1 H -[1,2,3]triazol-4-ylmethoxy)-3-methoxy-phenyl]-but-3-en-2-one ( 5 ); and 4-[4-(1-Benzyl-1 H -[1,2,3]triazol-4-ylmethoxy)-3-methoxy-phenyl]-4-hydroxy-butan-2-one ( 6 ), as well as the previously known derivative ( 7 ) were subjected to antimicrobial, antiquorum-sensing and cytotoxic evaluation. Compounds  4 – 7  possessed the most notable enhancement in the anti-bacterial activity against  Bacillus cereus ,  Pseudomonas aeruginosa  and antifungal activity against  Candida albicans . However, compounds  1  and  2  exhibited high antiquorum-sensing activity against  Chromobacterium violaceum  using catechin as a positive control. Compounds  4 – 7  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.

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