ISSN:
0170-2041
Keywords:
Pyrazolo[3,4-d]pyrimidine
;
Pyrazoles
;
2′-Deoxyribonucleosides
;
Glycosylation
;
Cytotoxicity
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201191
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