Anti-Hepatitis B Virus Activity of New N4-β-D-Glycoside Pyrazolo[3,4-d]pyrimidine Derivatives

Abstract

The reaction of 6-hydrazinyl-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione (1) with ethoxy-methylenemalononitrile afforded 5-amino-1-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyri-midin-6-yl)-1H-pyrazole-4-carbonitrile (2). The latter was reacted with formamide and urea affording the corresponding 4-aminopyrazolo[3,4-d]pyrimidines 3 and 4. The reaction of monosaccharide aldoses with 3 and 4 gave stereoselectively the β-N-glycosides 5a -- d and 6a -- d which were treated with acetic anhydride in pyridine to afford the corresponding acetylated derivatives 7a -- d and 8a -- d. The prepared compounds were tested for their anti-viral activity against hepatitis B virus (HBV) and showed moderate to high activities. © 2009, Verlag der Zeitschrift für Naturforschung. All rights reserved.