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Synthesis and Biological Evaluation of 4′‐ C ,3′‐ O ‐Propylene‐Linked Bicyclic Nucleosides
Author(s) -
Hatton Wilfried,
Hunault Julie,
Egorov Maxim,
Len Christophe,
Pipelier Muriel,
Blot Virginie,
Silvestre Virginie,
Fargeas Valérie,
Ané Adjou,
McBrayer Tami,
Detorio Mervi,
Cho JongHyun,
Bourgoug Nathalie,
Dubreuil Didier,
Schinazi Raymond F.,
Lebreton Jacques
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100859
Subject(s) - phosphoramidate , prodrug , nucleobase , pyrimidine , bicyclic molecule , combinatorial chemistry , stereochemistry , chemistry , ring closing metathesis , ring (chemistry) , metathesis , organic chemistry , dna , biochemistry , polymerization , polymer
A set of pyrimidine nucleosides fused with a 4′‐ C ,3′‐ O ‐propylene bridge was successfully synthesised in 12 steps from 1,2:5,6‐di‐ O ‐isopropylidene‐α‐ D ‐glucofuranose, an inexpensive starting material, based on a ring‐closing metathesis (RCM) reaction followed by Vorbrüggen‐type nucleobase coupling. Antiviral and cytotoxicity activities of the targeted modified nucleosides, as well as their phosphoramidate prodrugs, are described.