Nucleoside analogues play an important role in antiviral, antibacterial and antineoplastic chemotherapy. Herein we report the synthesis, structural characterization and biological activity of some 4′-C-methyl- and -phenyl dioxolane-based nucleosides. In particular, α and β anomers of all natural nucleosides were obtained and characterized by NMR, HR-MS and X-ray crystallography. The compounds were tested for antimicrobial activity against some representative human pathogenic fungi, bacteria and viruses. Antitumor activity was evaluated in a large variety of human cancer cell-lines. Although most of the compounds showed non-significant activity, 23α weakly inhibited HIV-1 multiplication. Moreover, 22α and 32α demonstrated a residual antineoplastic activity, interestingly linked to the unnatural α configuration. These results may provide structural insights for the design of active antiviral and antitumor agents.

Synthesis, structural characterization and biological evaluation of 4′-C-methyl- and phenyl-dioxolane pyrimidine and purine nucleosides / Franchini, Silvia; Battisti, Umberto M.; Sorbi, Claudia; Tait, Annalisa; Cornia, Andrea; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Loddo, Roberta; Madeddu, Silvia; Sanna, Giuseppina; Brasili, Livio. - In: ARCHIVES OF PHARMACAL RESEARCH. - ISSN 0253-6269. - 40:5(2017), pp. 537-549.

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