SYNTHESIS OF 6-CARBON, 7-CARBON AND 8-CARBON SUGAR ANALOGS OF POTENT ANTIINFLUENZA 2,3-DIDEHYDRO-2,3-DIDEOXY-N-ACETYLNEURAMINIC ACID-DERIVATIVES

Analogues of the potent anti-influenza A and B compound, 4-guanidino-N eu5Ac2en, are described in which the stereochemically demanding C-6-gl ycerol side-chain is truncated. Syntheses of the one- and two-carbon s ide-chain analogues, of both 4-guanidino- and 4-amino-Neu5Ac2en, are p resented, as well as the syntheses of analogues lacking any side-chain . Whilst complete removal of the C-6 side-chain abolishes activity, a stepwise increase in inhibition of influenza neuraminidase and influen za A and B in cell culture with increasing C-6 chain length is observe d. The one-carbon, hydroxymethyl derivative retains significant activi ty to represent a suitable lead in the search for neuraminidase inhibi tors of reduced stereochemical demand and synthetic complexity.