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Issue 26, 2017
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Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates

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Abstract

L-α-2′-Deoxythreosyl nucleoside phosphonates and their phosphonodiamidate prodrugs with a hypoxanthine, 2,6-diaminopurine, 2-amino-6-cyclopropylaminopurine, 7-deazaadenine, 5-fluorouracil and 5-methylcytosine heterocycle as a nucleobase were synthesized and evaluated for their inhibitory activity against HIV and HBV. The 2,6-diaminopurine modified analogue 23a displayed the most potent activity against HIV, with an EC50 value of 11.17 μM against HIV-1 (IIIB) and an EC50 value of 8.15 μM against HIV-2 (ROD). The application of the prodrug strategy on nucleoside phosphonate 23a led to a 200-fold boost in anti-HIV potency. None of the compounds showed any activity against HBV at the highest concentration tested.

Graphical abstract: Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates

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Publication details

The article was received on 23 May 2017, accepted on 08 Jun 2017 and first published on 19 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01265A
Citation: Org. Biomol. Chem., 2017,15, 5513-5528
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    Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates

    C. Liu, S. G. Dumbre, C. Pannecouque, B. Korba, S. De Jonghe and P. Herdewijn, Org. Biomol. Chem., 2017, 15, 5513
    DOI: 10.1039/C7OB01265A

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