Synthesis of α-fluoro- And α,α-difluoro- benzenemethanesulfonamides: New inhibitors of carbonic anhydrase

Article abstract of DOI:10.1039/b417327a

Direct fluorination of arenemethanesulfonamide anions under mild conditions and in high yield has been accomplished using N-fluorobisbenzenesulfonimide, NFSi, on carbanions of N-tert-butyl- and N-bis-(4-methoxyphenyl-methyl)- benzenemethanesulfonamides giving novel α-fluoro- and α,α- difluoro-benzenemethanesulfonamides respectively: IC₅₀ and pK _a data show that α-halogenation enhances sulfonamide acidity incrementally and correlates well with increased carbonic anhydrase inhibition, while lipophilicity is also enhanced.