78586-33-1Relevant academic research and scientific papers
C4-substituted 1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidines as adenosine agonist analogues.
Hamilton,Bristol
, p. 1601 - 1606 (2007/10/02)
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
Synthesis and Antiviral Activity of certain Carbamoylpyrrolopyrimidine and Pyrazolopyrimidine Nucleosides
Goebel, Richard J.,Adams, Alexander D.,McKernan, Patricia A.,Murray, Byron K.,Robins, Roland K.,et al.
, p. 1334 - 1338 (2007/10/02)
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.
