F. Oertel, H. Winter, Z. Kazimierczuk
Nov 20, 1992
Citations
0
Influential Citations
8
Citations
Journal
European Journal of Organic Chemistry
Abstract
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.