EnglishNucleoside 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.
| Data di pubblicazione: | 2017 |
| Titolo: | Synthesis, structural characterization and biological evaluation of 4′-C-methyl- and phenyl-dioxolane pyrimidine and purine nucleosides |
| Autore/i: | 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 |
| Autore/i UNIMORE: | |
| Digital Object Identifier (DOI): | 10.1007/s12272-016-0825-6 |
| Rivista: | |
| Volume: | 40 |
| Fascicolo: | 5 |
| Pagina iniziale: | 537 |
| Pagina finale: | 549 |
| Codice identificativo ISI: | WOS:000401721700001 |
| Codice identificativo Scopus: | 2-s2.0-85019629429 |
| Codice identificativo Pubmed: | 27615010 |
| Citazione: | 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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