Synthesis and biological evaluation of dinucleoside methylphosphonates of 3′-azido-3′-deoxythymidine and 2′, 3′-dideoxycytidine
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Add time:08/02/2019 Source:sciencedirect.com
The 5′ → 5′ dinucleoside methylphosphonates of 3′-azido-3′-deoxythymidine (AZT) and 2′,3′-dideoxycytidine (DDC) were prepared and evaluated for their inhibitory properties against different viruses, including human immunodeficiency virus (HIV). The synthesis of the compounds was achieved by reaction of AZT or N4-(4-monomethoxytrityl)-2′,3′-dideoxycytidine with in situ prepared methylphosphonic bis(triazolide), followed in the latter case by an acidic treatment. The two title compounds showed in vitro anti-HIV activity, that was 200- to 450-fold less pronounced than that shown by the corresponding monomeric nucleosides AZT and DDC. The decreased antiviral activity may be ascribed to nuclease resistance of the methylphosphonate linkage.
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