Studies on synthesis and biological activity of modified nucleoside and nucleotide
analogues have been an active field of research in medicinal chemistry for years
[1, 2]. High biological activity of naturally occurring C-nucleosides, for example
showdomycin 5, formycins A 41 and B 42 motivated many research groups to study
their analogues and structurally similar compounds. Furthermore, since C-nucleosides
lack N-glycosidic bond they are more resistant to enzymatic hydrolysis [3].
This review collects selected methods of synthesis of C-nucleoside analogues
which were analyzed to point out the most interesting and inspiring synthetic
strategies, in many cases based on contemporary achievements. These strategies
first of all take advantage of the formation of the C–C bond between the anomeric
carbon atom of the sugar or pseudosugar moieties and the carbon atom of the
modified nucleobases. Less common approach relies on the de novo construction
of heterocyclic rings employed as nucleobase substitutes. Though years many new
compounds sometimes of significant structural complexity have been obtained and
characterized to find several examples endowed with high antiviral and cytostatic
activity.
The biological activity of the C-nucleoside analogues screened so far encourages
us to continue a search for new potential drugs within compounds equipped
with this attractive structural motif.
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