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Synthesis of novel sulfonamido and 1, 2, 3-triazolyl reversed nucleoside derivatives

Recently, we have prepared a series of novel pyrimidine derivatives possessing a sulfonamide and a nucleobase pharmacophore, which exhibit strong antitumor activity.1, 2 As a part of our program directed toward the synthesis and characterization of biologically active nucleobase derivatives, we decided to synthesized sulfonamido II and 1, 2, 3-triazolyl derivatives III of reversed nucleosides. Based on our reported synthesis of "double headed" nucleosides3, 4 we prepared a series of C-5' substituted reversed nucleosides I. The introduction of the sulfonamido group at the C-1 position of the ribose was achieved using different sulfonamides and boron trifluoride etherate as the catalyst. We have also prepared novel 1, 2, 3-triazolyl reversed nucleoside derivatives III via suitable protected reversed nucleoside intermediates using 1, 4-regioselective copper-catalyzed azide/alkyne cycloaddition (CuAAC). The synthesis of the target nucleoside derivatives will be presented.

sulfonamido reversed nucleoside derivatives; 1; 2; 3-triazolyl reversed nucleoside derivatives

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