DOES THE ANTI-HEPATITIS-B VIRUS ACTIVITY OF (-5'-NORARISTEROMYCIN EXIST IN ITS 4'-EPIMER AND 4'-DEOXYGENATED DERIVATIVES())

To begin an exploration of the structural parameters responsible for t he activity of (+)-5'-noraristeromycin toward hepatitis B virus (HBV), three derivatives varied at the C-4' position have been prepared and evaluated. The syntheses began with a Mitsunobu coupling reaction of a n appropriate cyclopentanol with B-chloropurine. The products of these reactions were synthetically altered by standard ammonolysis and depr otection procedures to give the desired products. Evaluation of the ne w derivatives indicated that removal of the C-4' hydroxyl of (+)-5'-no raristeromycin increased its potency toward HBV by approximately 10-fo ld.