Medicinal Chemistry

Atta-ur-Rahman  
Honorary Life Fellow
Kings College
University of Cambridge
Cambridge
UK
Email: mc@benthamscience.org

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β-Glucuronidase Inhibitory Studies on Coumarin Derivatives

Author(s): Khalid Mohammed Khan, Muhammad Imran Fakhri, Nimra Naveed Shaikh, Syed Muhammad Saad, Shafqat Hussain, Shahnaz Perveen and Muhammad Iqbal Choudhary

Affiliation: H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan.

Keywords: β-glucuronidase, coumarin, Pechmann reaction, enzyme inhibition, β-glucuronidase related disorders, acid catalysis.

Graphical Abstract:


Abstract:

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.

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Article Details

VOLUME: 10
ISSUE: 8
Page: [778 - 782]
Pages: 5
DOI: 10.2174/1573406410666140311093352