Novel phosphate mimetics for the design of non-peptidyl inhibitors of protein tyrosine phosphatases

Benzylic α,α-difluorosulfonates, α,α-difluorotetrazoles, and α,α-difluorocarboxylates of type 5 and 6 were synthesized and examined as potential phosphate biosteres for PTP1B inhibition. The α,α-difluorosulfonates and α,α-difluorotetrazoles were found to be more effective inhibitors than the analogous compounds bearing the fluoromalonyl group, a phosphate biostere currently being used for PTP inhibition.