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EnglishAnew template of C-40-truncated phosphonated nucleosides (TPCOANs) has been obtained in good yields according to two different routes which exploit the reactivity of a phosphonated nitrone. The one-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl nucleobases leads to the unnaturalR-nucleosides as themain adducts.On the other hand, the target β-anomers have been obtained in high yield by a two-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl acetate followed by nucleosidation reaction. The reactivity of the phosphonated nitrone has been investigated trough quantummechanicalDFT calculations at the B3LYP/D95þ(d,p) theory level. Preliminary biological assays show that β-anomers of TPCOANs are able to inhibit the reverse trancriptase of different retroviruses at concentrations in the nanomolar range, with a potency comparable with that of tenofovir
| Titolo: | Synthesis of C-4’Truncated Phosphonated Carbocyclic 2’-Oxa-3’-azanucleosides as Antiviral Agents |
| Autori: | |
| Data di pubblicazione: | 2010 |
| Rivista: | |
| Abstract: | Anew template of C-40-truncated phosphonated nucleosides (TPCOANs) has been obtained in good yields according to two different routes which exploit the reactivity of a phosphonated nitrone. The one-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl nucleobases leads to the unnaturalR-nucleosides as themain adducts.On the other hand, the target β-anomers have been obtained in high yield by a two-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl acetate followed by nucleosidation reaction. The reactivity of the phosphonated nitrone has been investigated trough quantummechanicalDFT calculations at the B3LYP/D95þ(d,p) theory level. Preliminary biological assays show that β-anomers of TPCOANs are able to inhibit the reverse trancriptase of different retroviruses at concentrations in the nanomolar range, with a potency comparable with that of tenofovir |
| Handle: | http://hdl.handle.net/11570/1900845 |
| Appare nelle tipologie: | 14.a.1 Articolo su rivista |
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