Synthesis and Properties of Methylthiopyrazolo[3,4-d]pyrimidine 2′-Deoxy-β-D-ribonucleosides

Autor(en): Oertel, F.
Winter, H.
Kazimierczuk, Z.
Vilpo, J.A.
Richter, P.
Seela, F.
Stichwörter: 2′-Deoxyribonucleosides; Cytotoxicity; Glycosylation; Pyrazoles; Pyrazolo[3,4-d]pyrimidine
Erscheinungsdatum: 1992
Journal: Liebigs Annalen der Chemie
Volumen: 1992
Ausgabe: 11
Startseite: 1165
Seitenende: 1170
The synthesis of the 3- and 4-(methylthio)pyrazolo[3,4-d]pyrimidine N1- and N2-2′-deoxy-β-D-ribonucleosides 2b, 15 is described. Anionic glycosylation of 5-amino-3-(methylthio)-4-pyrazolecarbonitrile (4) or 4-(methylthio)pyrazolo[3,4-d]pyrimidine (12) with 2-deoxy-3,5-di-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl chloride (5) gave the regioisomeric N1-and N2-nucleosides 6, 7, 13, and 14. The N1 isomer was the main product in the reaction of 12, and the N2 compound was the preferred product in the glycosylation of 4. Glycosylation in suspension (12) yielded an appreciable amount of the N2 α-D-isomer 16. 4-Aminopyrazolo[3,4-d]pyrimidine 2′-deoxyribonucleosides 3a, b with a methylthio group at C-3 are resistant to deamination by adenosine deaminase and inhibit the proliferation of leukemia cell lines. Copyright © 1992 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN: 01702041
DOI: 10.1002/jlac.1992199201191
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