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KMID : 0043320170400050537
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Archives of Pharmacal Research
2017 Volume.40 No. 5 p.537 ~ p.549
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Synthesis, structural characterization and biological evaluation of 4′-C-methyl- and phenyl-dioxolane pyrimidine and purine nucleosides
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Franchini Silvia
Battisti Umberto M.
Sorbi Claudia
Tait Annalisa
Brasili Livio
Cornia Andrea
Jeong Lak-Shin
Lee Sang-Kook
Loddo Roberta
Madeddu Silvia
Sanna Giuseppina
Song Ja-Young
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Abstract
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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.
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KEYWORD
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Nucleosides, Antiviral, Antitumor, 1, 3-Dioxolanes, Pyrimidines, Purines, Vorbruggen reaction
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