Acta Pharm. 51 (2001) 63-73
Phase transfer catalysed epoxy alkylation of 1,2,5,6-di-O-isopropylidene-alpha- D-glucofuranose (2) with (±)-epichlorohydrin in aqueous/organic medium gave 3-O-epoxyalkyl derivative (3) as an intermediate. Upon reaction with secondary amines compound 3 gave 3-O-(2'-hydroxy-3'-aminopropyl) derivatives (4-9), which on selective deacetalisation in 4-7 gave the title compounds 3-O-(2'-hydroxy-3'-N,N-disubstituted aminopropane-1'-yl)-1,2-O- isopropylidene-alpha-D-glucofuranoses (10-13). The antiviral activity of the latter compounds was evaluated against Semliki forest virus (SFV), Japanese encephalitis virus (JEV) and encephalomyocarditis virus (EMCV) on vero cells as well as in the experimental mice. 3-O- (2'-hydroxy-3'-aminopropyl)-alpha-D-glucofuranoses with flexible beta-hydroxyadeninyl or guaninyl propyl chain exerted good antiviral activity against the enveloped viruses, SFS and JEV.
Keywords: alpha-D-glucofuranoses, synthesis, antiviral activity