A series of 1-glycosylmethyl-4,5-diphenyl-1H-imidazoles with six different glycosyls were obtained in 48-55% yields from the multicomponent reaction of the corresponding C-glycosyl methylamines, formaldehyde, benzil, and ammonium acetate under catalysis with indium(III) chloride in methanol at ambient temperature. Starting with C-β-d-glucopyranosyl or C-β-d-galactopyranosyl methylamines, the procedure also was examined with phenylglyoxal or glyoxal instead of benzil, and the pertinent 1-β-d-glycopyranosylmethyl-4-phenyl-1H-imidazole and -5-phenyl-1H-imidazole or 1-β-d-glycopyranosylmethyl-1H-imidazole derivatives were prepared and isolated. Of four differently 4- and 5-substituted 1-(β-d-glucopyranosylmethyl)-1H-imidazoles, only the 5-phenyl derivative exhibited a weak inhibition of rabbit muscle glycogen phosphorylase b (IC50=125 μM).
- C-Glycosyl methylamines
- Indium(III) chloride catalysis
- Multicomponent reaction
- Rabbit muscle glycogen phosphorylase inhibition
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry