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. 1983 Feb 11;11(3):871–882. doi: 10.1093/nar/11.3.871

A convenient synthesis of 6-amino-1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4-one and related 4,6-disubstituted pyrazolopyrimidine nucleosides.

H B Cottam, G R Revankar, R K Robins
PMCID: PMC325758  PMID: 6835838

Abstract

The glycosylation of 4,6-dichloropyrazolo[3,4-d]pyrimidine and 4-chloro-6-methylthiopyrazolo[3,4-d]pyrimidine via the corresponding trimethylsilyl intermediate and tetra-O-acetyl-beta-D-ribofuranose in the presence of trimethylsilyl triflate as a catalyst, gave selective glycosylation at N1 as the only nucleoside product. The intermediates 4,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)pyrazolo [3,4-d]pyrimidine 7 and 4-chloro-6-methylthio-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)pyrazolo [3,4-d]pyrimidine 13 gave new and convenient synthetic routes to the inosine analog 1, the guanosine analog 2, the adenosine analog 3, and the isoguanosine analog 16. Glycosylation of the trimethylsilyl derivative of 6-chloropyrazolo[3,4-d]pyrimidine-4-one unexpectedly gave the N2-glycosyl isomer 20 as the major product. A number of new 4,6-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides were prepared from these glycosyl intermediates.

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Selected References

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  1. Avila J. L., Avila A. Trypanosoma cruzi: allopurinol in the treatment of mice with experimental acute Chagas disease. Exp Parasitol. 1981 Apr;51(2):204–208. doi: 10.1016/0014-4894(81)90109-0. [DOI] [PubMed] [Google Scholar]
  2. Berens R. L., Marr J. J., Nelson D. J., LaFon S. W. Antileishmanial effect of allopurinol and allopurinol ribonucleoside on intracellular forms of Leishmania donovani. Biochem Pharmacol. 1980 Sep 1;29(17):2397–2398. doi: 10.1016/0006-2952(80)90275-0. [DOI] [PubMed] [Google Scholar]
  3. CLAYTON C. LEGAL ASSESSOR'S DUTIES. Lancet. 1964 Jan 25;1(7326):215–215. doi: 10.1016/s0140-6736(64)92308-6. [DOI] [PubMed] [Google Scholar]
  4. Dewey V. C., Kidder G. W. Inhibitory action of the adenine analog, 4-aminopyrazolo(3,4-d)pyrimidine, in Crithidia fasciculata. Can J Biochem. 1977 Jan;55(1):110–112. doi: 10.1139/o77-017. [DOI] [PubMed] [Google Scholar]
  5. LaFon S. W., Nelson D. J., Berens R. L., Marr J. J. Purine and pyrimidine salvage pathways in Leishmania donovani. Biochem Pharmacol. 1982 Jan 15;31(2):231–238. doi: 10.1016/0006-2952(82)90216-7. [DOI] [PubMed] [Google Scholar]
  6. Nelson D. J., LaFon S. W., Tuttle J. V., Miller W. H., Miller R. L., Krenitsky T. A., Elion G. B., Berens R. L., Marr J. J. Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation. J Biol Chem. 1979 Nov 25;254(22):11544–11549. [PubMed] [Google Scholar]
  7. Revankar G. R., Townsend L. B. Pyrazolopyrimidine nucleosides. Part I. Synthesis of pyrazolopyrimidine nucleosides related to the nucleoside antibiotic tubercidin. J Chem Soc Perkin 1. 1971;13:2440–2442. doi: 10.1039/j39710002440. [DOI] [PubMed] [Google Scholar]
  8. Rideout J. L., Krenitsky T. A., Koszalka G. W., Cohn N. K., Chao E. Y., Elion G. B., Latter V. S., Williams R. B. Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 2. Synthesis and activity of some nucleosides of 4-(alkylamino)-1H-pyrazolo[3, 4-d]pyrimidines. J Med Chem. 1982 Sep;25(9):1040–1044. doi: 10.1021/jm00351a007. [DOI] [PubMed] [Google Scholar]

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