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Synthesis of 3-substituted 4-methylmercapto- and 4-aminopyrazolo-[3,4-d]pyrimidines and their ribosides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Cyano-4-methylmercaptopyrazolo[3,4-d]pyrimidine, fusion of which with 1,2,3,5-tetra-0-acetyl-β-D-ribofuranose gave its per-0-acetylated 1-β-D-ribofuranoside in 61% yield, was synthesized from 3,4-dicyano-5-aminopyrazole. 0-Deacetylation of the per-0-acetylated 1-β-D-ribofuranoside was carried out by the action of 1% HCl in methanol. New pyrazolo[3,4-d]pyrimidines were obtained by the reaction of 3-cyano-4-methylmercaptopyrazolo[3,4-d]pyrimidine and its 1-riboside, as well as 3-cyano-4-aminopyrazolo[3,4-d]pyrimidine, with a number of nucleophilic reagents. The cytotoxic activities of the compounds obtained were studied.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 253–258, February, 1984.

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Bulychev, Y.N., Korbukh, I.A. & Preobrazhenskaya, M.N. Synthesis of 3-substituted 4-methylmercapto- and 4-aminopyrazolo-[3,4-d]pyrimidines and their ribosides. Chem Heterocycl Compd 20, 210–215 (1984). https://doi.org/10.1007/BF00506295

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  • DOI: https://doi.org/10.1007/BF00506295

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