Abstract
Amongst all synthetic nucleosides having high potential biological activities, C5-modified pyrimidines and C7-deaza or C8-modified purines have been particularly studied. These main chemical modifications have been developed using palladium cross-coupling reactions. This review focus on both Heck and Sonogashira cross-coupling of nucleosides using different aspects of the twelve principles of green chemistry: use of aqueous medium and no protection/deprotection steps.
Highlights
Amongst all synthetic nucleosides having high potential biological activities, C5-modified pyrimidines and C7-deaza or C8-modified purines have been studied
[7,12,13,14,15], this paper will focused on the Heck reactions and Sonogashira reactions applied to unprotected nucleosides and nucleotides in aqueous media or water as sole solvent
The first Heck cross-coupling reaction starting from deprotected nucleoside was reported in 1998 by Barbas et al [16]
Summary
Amongst all synthetic nucleosides having high potential biological activities, C5-modified pyrimidines and C7-deaza or C8-modified purines have been studied. These main chemical modifications have been developed using palladium cross-coupling reactions. Among all the potent modifications, introduction of aryl, polyaryl, heteroaryl, heteropolyaryl, alkenyl and alkynyl groups on either the pyrimidine or the purine moiety via C-C cross-coupling was described for the study of biological environments such as DNA and RNA structural probes, protein–DNA complexes, DNA damage, mutation and cancers [10,11]. The first Heck cross-coupling reaction starting from deprotected nucleoside was reported in 1998 by Barbas et al [16].
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