Moon Woo Chun

Synthesis and Antiviral Activity of D- and L-Isodideoxy Nucleosides with Exocyclic Methylene

Novel D- and L-isodideoxynucleosides were synthesized starting from D- and L-xylose and evaluated for antiviral activities against HIV-1, HSV-1, HSV-2, HBV and HCMV, respectively.

STEREOSELECTIVE SYNTHESIS OF CONFORMATIONALLY RIGID APIO CARBANUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS

Apio north-methanocarbocyclic nucleosides 1–3 with bicyclo[3.1.0]hexane template were first synthesized. Introduction of hydroxymethyl substituent was efficiently and stereoselectively accomplished by aldol and retro-aldol reaction and fixed conformation was achieved from a modified Simmons-Smith cyclopropanation on a cyclopentane ring.

Participation of sulfur occurred during the Mitsunobu reaction: synthesis of novel isodideoxythionucleosides

Novel isodideoxythionucleosides have been synthesized from our versatile intermediate, L-4-thioarabitol derivative 5 using the Mitsunobu reaction as a key step. It is found that the sulfur atom of the 4-thiofuranose derivative takes part in the Mitsunobu reaction.

Design, Synthesis, and Anti-Tumor Activity of 4′-Thionucleosides as Potent and Selective Agonists at the Human A3 Adenosine Receptor

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-N 6-(3-iodobenzyl)- and 2-chloro-N 6-methyl-4′ -thioadenosine-5′ -methyluronamides (7a and 7b) exhibited nanomolar range of binding affinity (K i = 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.

D-4'-thioadenosine derivatives as highly potent and selective agonists at the human A3 adenosine receptor.

4′-Thionucleoside derivatives as potent and selective A3 adenosine receptor agonists were synthesized, starting from d-gulono-γ-lactone via d-thioribosyl acetate as a key intermediate, among which the 2-chloro-N6-methyladenosine-5′-methyluronamide showed the most potent and selective binding affinity (Ki=0.28±0.09 nM) at the human A3 adenosine receptor.