Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates | Zendy

Chao Liu | Zendy; Shrinivas G. Dumbre | Zendy; Christophe Pannecouque | Zendy; Brent E. Korba | Zendy; Steven De Jonghe | Zendy; Piet Herdewijn | Zendy

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Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates

Author(s) -

Chao Liu,

Shrinivas G. Dumbre,

Christophe Pannecouque,

Brent E. Korba,

Steven De Jonghe,

Piet Herdewijn

Publication year - 2017

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c7ob01265a

Subject(s) - chemistry , nucleoside , base (topology) , combinatorial chemistry , nucleoside analogue , stereochemistry , mathematical analysis , mathematics

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 EC 50 value of 11.17 μM against HIV-1 (III B ) and an EC 50 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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