Abstract
Abstract Synthetic nucleoside 5′-(α-halo)thioethers and derived 5′-halo(methylene) compounds function as potent mechanism-based inhibitors of S-adenosyl-L-homocysteine hydrolase. Nucleoside 5′-carboxaldehydes have been converted into 6′-tosyl(vinyl) derivatives. Radical-mediated stannyldesulfonylation of these homonucleoside vinyl sulfones gave 6′-stannyl(vinyl) derivatives. Stereoselective halodestannylation with electrophiles gave the 6-halo(homovinyl)nucleoside analogues. Some of these nucleoside analogue types have inhibitory activity against enzymes in the nucleic acid biochemical manifold and these effects correlate with in vitro anticancer and antiviral activities in certain cases.
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