(Halogenomethyl)phenyl α- D -glucopyranosides as enzyme-activated irreversible inhibitors of yeast α-glucosidase and potential anti-HIV agents

A range of (halogenomethyl)phenyl α-D-glucopyranosides 2–7, prepared from corresponding methylphenyl glucosides by synthetic manipulation of the aglycone moiety, have been investigated as enzyme-activated irreversible inhibitors of yeast α-glucosidase and their anti-HIV activity measured. Compounds 5–7, which also contain a 4- or 6-nitro group in the phenyl ring of the aglycone, are much more effective inhibitors of the enzyme than are compounds 2–4 which lack this feature.