Literature DB >> 28163339

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

Ozkan Sari1, Leda Bassit1, Christina Gavegnano1, Tamara R McBrayer2, Louise McCormick1, Bryan Cox1, Steven J Coats2, Franck Amblard1, Raymond F Schinazi1.   

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.

Entities:  

Keywords:  Antiviral; Fluorine; Mitsunobu; Nucleoside; Prodrug

Year:  2017        PMID： 28163339      PMCID： PMC5289701          DOI： 10.1016/j.tetlet.2017.01.006

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  18 in total

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