8-Aza-1-deazapurine nucleosides as antiviral agents

Article abstract of DOI:10.1080/15257779408009477

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.

Full text of DOI:10.1080/15257779408009477

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Nucleosides and Nucleotides
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8-Aza-1-deazapurine Nucleosides as
Antiviral Agents
P. Franchetti a , L. Messini a , L. Cappellacci a , G. Abu Sheikha a
,
M. Grifantini a , P. Guarracino b , A. De Montis b , A. G. Loi b , M. E.
Marongiu b & P. La Colla b
a Dipartimento di Scienze Chimiche , Università di Camerino , 62032,
Camerino
b Dipartimento di Biologia Sperimentale , Universita di Cagliari ,
09124, Cagliari, Italy
Published online: 24 Sep 2006.
To cite this article: P. Franchetti , L. Messini , L. Cappellacci , G. Abu Sheikha , M. Grifantini ,
P. Guarracino , A. De Montis , A. G. Loi , M. E. Marongiu & P. La Colla (1994) 8-Aza-1-
deazapurine Nucleosides as Antiviral Agents, Nucleosides and Nucleotides, 13:8, 1739-1755, DOI:
10.1080/15257779408009477
To link to this article: http://dx.doi.org/10.1080/15257779408009477
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