2-L-Rhamnopyranosyl[1,2,4]triazolo[1,5-a]pyridine. 4' and 3' Oxidation products. Synthesis and structure-activity relationships

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Abstract
A series of 2-.alpha.-L-rhamnopyranosylnitro[1,2,4]triazolo[1,5-a]pyridine C-nucleosides was synthesized from the condensation of a thioiminoether with nitro-2-pyridylhydrazines. Catalytic reducion afforded the corresponding amino derivative. A 1'',2'' unsaturated C-nucleoside was also obtained by 2 different routes. Selective oxidation gave the 3''- and 4''-ketonucleosides. The cytotoxic properties of the nucleosides and their effect on viral transformation and replication were described. The nitro derivatives inhibit viral replication, but at toxic doses; the introduction of a keto function leads to a product which inhibits the replication of murine leukemia virus (MuLV) at noncytotoxic concentrations. The amino derivatives have no significant antiviral effect.