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Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides.

ABSTRACT: A series of 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4'-azanucleosides were prepared as a separable mixture of ?- and ?-anomers. The 6-chloropurine analogue was obtained as a mixture of N(7) and N(9) regioisomers and their structures were identified based on NOESY and HMBC spectral data. Among the 4'-azanucleosides tested as HIV-1 inhibitors in primary human lymphocytes, four compounds showed modest activity and the 5-fluorouracil analogue (18d) was found to be the most active compound (EC(50)=36.9?M) in this series. None of the compounds synthesized in this study demonstrated anti-HCV activity.

SUBMITTER: Martinez-Montero S 

PROVIDER: S-EPMC3489957 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides.

Martínez-Montero Saúl S   Fernández Susana S   Sanghvi Yogesh S YS   Theodorakis Emmanuel A EA   Detorio Mervi A MA   McBrayer Tamara R TR   Whitaker Tony T   Schinazi Raymond F RF   Gotor Vicente V   Ferrero Miguel M  

Bioorganic & medicinal chemistry 20120923 23

A series of 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4'-azanucleosides were prepared as a separable mixture of α- and β-anomers. The 6-chloropurine analogue was obtained as a mixture of N(7) and N(9) regioisomers and their structures were identified based on NOESY and HMBC spectral da  ...[more]

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