- Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication
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A variety of 2,6-modified purine 2′-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.
- Zhou, Longhu,Zhang, Hongwang,Tao, Sijia,Ehteshami, Maryam,Cho, Jong Hyun,McBrayer, Tamara R.,Tharnish, Philip,Whitaker, Tony,Amblard, Franck,Coats, Steven J.,Schinazi, Raymond F.
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supporting information
p. 17 - 22
(2016/02/03)
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- A short, flexible route toward 2'-C-branched ribonucleosides
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A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.
- Harry-O'kuru,Smith,Wolfe
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p. 1754 - 1759
(2007/10/03)
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- 2′-C-alkylribonucleosides: Design, synthesis, and conformation
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Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright
- Harry-O'kuru, Rogers E.,Kryjak, Emily A.,Wolfe, Michael S.
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p. 1457 - 1460
(2007/10/03)
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- A concise synthesis of 2'-C-methylribonucleosides
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2'-C-methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-α-D-ribose with good overall yields.
- Wolfe,Harry-O'kuru
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p. 7611 - 7614
(2007/10/02)
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