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Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates.

Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates.
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Liu C, Dumbre SG, Pannecouque C, Korba B, De Jonghe S, Herdewijn P,


Liu C, Dumbre SG, Pannecouque C, Korba B, De Jonghe S, Herdewijn P, (click to view)

Liu C, Dumbre SG, Pannecouque C, Korba B, De Jonghe S, Herdewijn P,

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Organic & biomolecular chemistry 15(26) 5513-5528 doi 10.1039/c7ob01265a

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.

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