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Synthesis and antiviral evaluation of 2',2',3',3'-tetrafluoro nucleoside analogs.

ABSTRACT: Herein, we report the synthesis of novel 2',2',3',3'-tetrafluorinated nucleoside analogs along with their phosphoramidate prodrugs. A tetrafluoro ribose moiety was coupled with different Boc/benzoyl-protected nucleobases under Mitsunobu conditions. After deprotection, tetrafluorinated nucleosides 13b, 14b, 20b-22b were reacted with phenyl-(isopropoxy-L-alaninyl)-phosphorochloridate to afford corresponding monophosphate prodrugs 24b-28b. All synthesized compounds were evaluated against several DNA and RNA viruses including HIV, HBV, HCV, Ebola and Zika viruses.

SUBMITTER: Sari O

PROVIDER: S-EPMC5289701 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Synthesis and antiviral evaluation of 2',2',3',3'-tetrafluoro nucleoside analogs.

Sari Ozkan O Bassit Leda L Gavegnano Christina C McBrayer Tamara R TR McCormick Louise L Cox Bryan B Coats Steven J SJ Amblard Franck F Schinazi Raymond F RF

Tetrahedron letters 20170104 7

Herein, we report the synthesis of novel 2',2',3',3'-tetrafluorinated nucleoside analogs along with their phosphoramidate prodrugs. A tetrafluoro ribose moiety was coupled with different Boc/benzoyl-protected nucleobases under Mitsunobu conditions. After deprotection, tetrafluorinated nucleosides 13b, 14b, 20b-22b were reacted with phenyl-(isopropoxy-L-alaninyl)-phosphorochloridate to afford corresponding monophosphate prodrugs 24b-28b. All synthesized c ...[more]

PMID: 28163339

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