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Synthesis and anti-HIV activity of guanine modified fluorinated acyclic nucleoside phosphonates derivatives



Synthesis and anti-HIV activity of guanine modified fluorinated acyclic nucleoside phosphonates derivatives



Chemistry and Biodiversity 2018



The preparation of an unprecedented series of nucleobase modified 3-fluoro-2-(phosphonomethoxy)propyl (FPMP) acyclic nucleosides in both their (R) and (S) enantiomerically pure forms is described. The synthesis focuses on a Mitsunobu alkylation reaction to construct the C-N9 bond between a chiral fluorinated side-chain residue and 6- or 7-modified guanine analogues. Prodrugs of FPMP-7-deazaguanine were also synthesized by derivatization of the corresponding phosphonic acid functionality with (bis)diamyl aspartate amidate groups, leading to moderate activity against human immunodeficiency virus type 1 (HIV-1).

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Accession: 065930677

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PMID: 30431702

DOI: 10.1002/cbdv.201800532


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