Sm. Siddiqi et al., 3-DEAZA-5'-NORARISTEROMYCIN AND 7-DEAZA-5'-NORARISTEROMYCIN AND THEIRANTIVIRAL PROPERTIES, Journal of medicinal chemistry, 38(6), 1995, pp. 1035-1038
An enantiospecific synthesis of 3-deaza-5'noraristeromycin as its dihy
drochloride ((-)-6) has been accomplished in six steps beginning with
the reaction of (+)-(1R,4S)d-hydroxy-2-cyclopenten-1-yl acetate with 4
-chloro-1H-imidazo[4,5-c]pyridine. The preparation of 7-deaza-5'-norar
isteromycin ((-)-7) was described previously. Compounds (-)-6 and (-)-
7 were evaluated for antiviral activity against a large number of viru
ses. Compound (-)-6 produced an antiviral activity pattern similar to
5'-noraristeromycin but was less potent. Compound (-)-6 inhibited CEM
cell proliferation at a 50% inhibitory concentration of 27 mu g/mL but
proved not inhibitory to HEL cell proliferation and not toxic to E(6)
SM, HeLa, Vero, and MDCK cells at concentrations up to 200 mu g/mL. Wh
ile (-)-6 showed inhibition of S-adenosyl-L-homocysteine (AdoHcy) hydr
olase, it was less inhibitory than 5'-noraristeromcyin. Compound(-)-7
displayed no antiviral properties or inhibitory effects toward AdoHcy
hydrolase.