Twenty-three (23) derivatives of coumarin (5-27) were synthesized and screened for their in vitro β-
glucuronidase (E. coli) inhibitory activities. Only three compounds, 7,8-dihydroxy-4-methyl-2H-chromen-2-one (9) (IC50
= 52.39 ± 1.85 µM), 3-chloro-6-hexyl-7-hydroxy-4-methyl-2H-chromen-2-one (18) (IC50 = 60.50 ± 0.87 µM), and 3,6-
dichloro-7-hydroxy-4-methyl-2H-chromen-2-one (15) (IC50 = 380.26 ± 0.92 µM) displayed activities against β-
glucuronidase as compared to standard D-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 µM). The results indicated that
the activity of the synthetic coumarins depends upon the substituents present on the coumarin skeleton.
Keywords: β-glucuronidase, coumarin, Pechmann reaction, enzyme inhibition, β-glucuronidase related disorders, acid catalysis.
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