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

✍ Scribed by Oertel, Frank ;Winter, Holger ;Kazimierczuk, Zygmunt ;Vilpo, J. A. ;Richter, Peter ;Seela, Frank

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
549 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The synthesis of the 3‐ and 4‐(methylthio)pyrazolo[3,4‐d]pyrimidine N^1^‐ and N^2^‐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 N^1^‐and N^2^‐nucleosides 6, 7, 13, and 14. The N^1^ isomer was the main product in the reaction of 12, and the N^2^ compound was the preferred product in the glycosylation of 4. Glycosylation in suspension (12) yielded an appreciable amount of the N^2^ 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.

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