N^α-arylsulfonyl histamines as selective β-glucosidase inhibitors (original) (raw)

N a-benzenesulfonylhistamine, a new semi-synthetic b-glucosidase inhibitor, was obtained by bioactivityguided isolation from a chemically engineered extract of Urtica urens L. prepared by reaction with benzenesulfonyl chloride. In order to identify better b-glucosidase inhibitors, a new series of N a ,N s-diarylsulfonyl and N a-arylsulfonyl histamine derivatives was prepared. Biological studies revealed that the b-glucosidase inhibition was in a micromolar range for several N a-arylsulfonyl histamine compounds of the series, N a-4-fluorobenzenesulfonyl histamine being the most powerful compound. Besides, this reversible and competitive inhibitor presented a good selectivity for b-glucosidase with respect to other target enzymes including a-glucosidase.