A cyclic analogue 4 of galardin, a known MMP inhibitor, is designed to improve its selectivity. The synthesis of 4 starts from dimethyl (S)-malate using diaselective alkylation and subsequent cyclization and amide formation as key steps. The compound 4 showed MMP inhibitory activity on all MMPs tested with IC50 ranging from 20.1 μM to 104 μM.
- Matrix metalloproteinases inhibitor
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