Synthesis, structure, and antiparasitic activity of sulfamoyl derivatives of ribavirin

The triazole nucleoside derivatives 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-carboxamide (2), 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-thiocarboxamide (3), and 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl)-[1,2,4]triazole-3- carbonitrile (4) were synthesize...

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Veröffentlicht in:Journal of medicinal chemistry 1990-01, Vol.33 (1), p.44-48
Hauptverfasser: Kini, Ganesh D, Henry, Elizabeth M, Robins, Roland K, Larson, Steven B, Marr, J. Joseph, Berens, Randolph L, Bacchi, Cyrus J, Nathan, Henry C, Keithly, Jan S
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Sprache:eng
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Zusammenfassung:The triazole nucleoside derivatives 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-carboxamide (2), 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-thiocarboxamide (3), and 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl)-[1,2,4]triazole-3- carbonitrile (4) were synthesized. Suitably protected triazole nucleosides were converted to their corresponding 5'-sulfamoyl derivatives, which on subsequent deprotection gave the desired compounds in good yields. The structures of compounds 2-4 were confirmed by X-ray crystallographic analysis. All three compounds showed significant antiparasitic activity in vitro, while 2 showed significant activity in vivo against Leishmania donovani and Trypanosoma brucei.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00163a008