Journal of Medicinal Chemistry p. 2127 - 2130 (1990)
Update date:2022-08-03
Topics:
Henry, Elizabeth M.
Kini, Ganesh D.
Larson, Steven B.
Robins, Roland K.
Alaghamandan, Hassan A.
Smee, Donald F.
2,6,8-Trichloro-7-methylpurine (3) was converted to 2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one (5) by utilizing the difference in reactivity of the 2-, 6-, and 8-positions in the trichloropurine ring system to nucleophilic displacement.Compound 5 was subsequently glycosylated with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose according to the Vorbrueggen procedure to yield 2-chloro-8,9-dihydro-7-methyl-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-8-thioxopurin-6(1H)-one (6).Removal of the benzoyl protecting groups, followed by amination of 7 with liquid ammonia at 150 deg C, gave 7,8-dihydro-7-methyl-8-thioxoguanosine (2).The structure of compound 2 was confirmed by X-ray crystallographic analysis.Compounds 1 (7,8-dihydro-7-methyl-8-oxoguanosine) and 2 were evaluated for activity in various animal virus infection models.Against banzi, Semliki Forest, and San Angelo viruses in mice, 2 was highly active when administered before virus inoculation.
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