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On the basis of potent and selective binding affinity of Cl-IB-MECA to the human A3 adenosine receptor, its 4'-thioadenosine derivatives were efficiently synthesized starting from D-gulonic γ -lactone. Among compounds tested, 2-chloro-N6-(3-iodobenzyl)- and 2-chloro-N6-methyl-4' -thioadenosine-5' -methyluronamides (7a and 7b) exhibited nanomolar range of binding affinity (Ki = 0.38 nM and 0.28 nM, respectively) at the human A3AR. These compounds showed anti-growth effects on HL-60 leukemia cell, which resulted from the inhibition of Wnt signaling pathway. [ABSTRACT FROM AUTHOR]

Stereoselective functionalization of the 1'-position of 4'-thionucleosides was achieved using a stereoselective SN2 reaction controlled by 5-membered ring coordination. [ABSTRACT FROM AUTHOR]