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In the presented study, eight novel Meldrum’s acid derivatives containing various vanillic groups were synthesized. Vanillidene Meldrum’s acid compounds were tested against different cancer cell lines and microbes. Out of nine, three showed very good biological activity against <i>E. coli</i>, and HeLa and A549 cell lines. It is shown that the <i>O</i>-alkyl substituted derivatives possessed better antimicrobial and anticancer activities in comparison with the <i>O</i>-acyl ones. The decyl substituted molecule (<b>3i</b>) has the highest activity against <i>E. coli</i> (MIC = 12.4 μM) and cancer cell lines (HeLa, A549, and LS174 = 15.7, 21.8, and 30.5 μM, respectively). The selectivity index of <b>3i</b> is 4.8 (HeLa). The molecular docking study indicates that compound <b>3i</b> showed good binding affinity to DNA, <i>E. coli</i> Gyrase B, and topoisomerase II beta. The covalent docking showed that <b>3i</b> was a Michael acceptor for the nucleophiles Lys and Ser. The best E_b was noted for the topoisomerase II beta-LYS482-<b>3i</b> cluster.