162299-73-2Relevant academic research and scientific papers
8-Aza-1-deazapurine nucleosides as antiviral agents
Franchetti,Messini,Cappellacci,Abu Sheikha,Grifantini,Guarracino,De Montis,Loi,Marongiu,La Colla
, p. 1739 - 1755 (1994)
2',3'-Dideoxy-8-aza-1-deazaadenosine (21) and its α-anomer (20) were synthesized via glycosylation of 7-chloro-3H-1,2,3-triazolo[4,5-b]pyridine with 2,3-dideoxy-5-O-[(1,1)-dimethylethyl)diphenylsilyl]-D-glycero- pentofuranosyl chloride. The reaction gave a mixture of α- and β-anomers of N3-, N2- and N1-glycosylated regioisomers (12-15). The α- and β-anomers of the N4-glycosylated isomer 26 and 27 were also synthesized through the glycosylation of 8-aza-1-deazaadenine with 1-acetoxy-2,3-dideoxy-5-O-[(1,1- dimethylethyl)dimethylsilyl]-D-glycero-pentofuranose. These dideoxynucleosides and a series of previously synthesized 8-aza-1-deazapurine nucleosides were tested for activity against several DNA and RNA viruses, HIV-1 included. The α- and β-anomers of 7-chloro-3-(2-deoxy-D-erythro- pentofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (3a and 4) showed activities against Sb-1 and Coxs viruses. The α- and β-anomers of 2',3'-dideoxy-8- aza-1-deazaadenosine (20 and 21) were found active as inhibitors of adenosine deaminase.
