- C4-substituted 1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidines as adenosine agonist analogues.
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The synthesis of four novel C4-substituted 1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidines is reported, and the compounds were examined as adenosine receptor agonist analogues. Neither receptor affinity nor biological activity was as potent as the purine
- Hamilton,Bristol
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p. 1601 - 1606
(2007/10/02)
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- Synthesis and Antiviral Activity of certain Carbamoylpyrrolopyrimidine and Pyrazolopyrimidine Nucleosides
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Following our recent discovery that 9-β-D-ribofuranosylpurine-6-carboxamide (1) exhibits potent antiviral activity, we were prompted to synthesize certain pyrrolopyrimidine and pyrazolopyrimidine nucleoside containing a carbamoyl function (7a,b and 13).The key precursor, 7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolopyrimidine-4-carbonitrile (8a), required for the synthesis of 7a was prepared from the corresponding 4-chloro analogue (4a).Reaction of 4a with methanethiol, followed by oxidation, gave the 4-methylsulfonyl derivative (6a), which with NaCl in DMF gave 8a.Alkaline hydrolysis of 8a provided 7a.Similarly, 7b was prepared from 4-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolopyrimidine (4b) via the carbonitrile intermediate 8b.Starting with thioformycin B or 7-chloro-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolopyrimidine (10) and following the similar sequence of reactions, we obtained compound 13.The in vitro antiviral studies of these carbamoyl and certain related nucleosides indicated 7a to be a potent antiviral agent against vaccinia virus, whereas 13 was moderately active. 4-Chloro-7-β-D-ribofuranosylpyrrolopyrimidine was found to be one of the most active compounds against RVF, PICH, YF, and SF viruses in culture.
- Goebel, Richard J.,Adams, Alexander D.,McKernan, Patricia A.,Murray, Byron K.,Robins, Roland K.,et al.
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p. 1334 - 1338
(2007/10/02)
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