Abstract
2-Amino-9-β-D-ribofuranosylpurine-2-sulfonamide (2-sulfamoyladenosine, 4), a congener of sulfonosine (3), was synthesized by four different routes. Acid catalyzed fusion of 6-chloropurine-2-sulfonyl fluoride (5) with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (8) gave a good yield of 6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine-2-sulfonyl fluoride (9). Ammonolysis of 9 furnished 4. Lewis acid catalyzed glycosylation of the trimethylsilyl derivative of either 6-chloropurine-2-sulfonamide (6) or 6-aminopurine-2-sulfonamide (7) with 8 gave the corresponding N9-glycosylated products, 10 and 11, respectively, which on ammonolysis gave 4. Amination of 2-thioadenosine (12) with chloramine solution gave the sulfenamide derivative 13, which on subsequent oxidation with m-chloroperoxybenzoic acid furnished an alternate route to 4. The structure of 4 was established by single-crystal X-ray diffraction studies. 2-Sulfamoyladenosine (4) is devoid of significant inhibitory activity against L1210 leukemia in mice.
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