Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents

Abstract

Summary Analogues of 4-guanidino-Neu5Ac2en (GG167) have been prepared containing alternative amide and sulfonamide substituents at the 5-position. (4 S ,5 R ,6 R )-4-guanidino-5-(2,2,2-trifluoroacetylamino)-6-(1 R ,2 R , 3-trihydroxypropyl)-5,6-dihydro-4 H -pyran-2-carboxylic acid 5 and (4 S ,5 R ,6 R )-4-guanidino-5-methanesulfonylamino-6-(1 R ,2 R ,3-trihydroxypropyl)-5, 6-dihydro-4 H -pyran-2-carboxylic acid 6 were the only analogues which approached the activity of GG167, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.