Anti-hepatitis B virus activity of new N4-beta-D-glycoside Pyrazolo [3,4-d]pyrimidine derivatives.
The reaction of 6-hydrazinyl-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione (1) with ethoxymethylenemalononitrile afforded 5-amino-1-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-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 beta-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 antiviral activity against hepatitis B virus (HBV) and showed moderate to high activities.
El-Sayed
Wael A
WA
Photochemistry Department, National Research Center, El Dokki, Cairo, Egypt. waelshendy@gmail.com
Ramiz
Mahmoud M M
MM
Abdel-Rahman
Adel A-H
AA
D000107:Acetylation; D000215:Acylation; D000998:Antiviral Agents / Q000494:pharmacology* / Q000627:therapeutic use; D006027:Glycosides / Q000494:pharmacology; D006509:Hepatitis B / Q000188:drug therapy*; D006515:Hepatitis B virus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D011720:Pyrazoles / Q000494:pharmacology*; D011743:Pyrimidines / Q000494:pharmacology*; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D006027:Glycosides; D011720:Pyrazoles; D011743:Pyrimidines