SYNTHESIS AND PROPERTIES OF METHYLTHIOPYRAZOLO[3,4-D]PYRIMIDINE 2'-DEOXY-BETA-D-RIBONUCLEOSIDES

Autor(en): OERTEL, F
WINTER, H
KAZIMIERCZUK, Z
VILPO, JA
RICHTER, P
SEELA, F
Stichwörter: 2'-DEOXYRIBOFURANOSIDES; 2'-DEOXYRIBONUCLEOSIDES; ALLOPURINOL; BIOLOGICAL-ACTIVITY; Chemistry; Chemistry, Multidisciplinary; CYTOTOXICITY; GLYCOSYLATION; NUCLEOSIDES; PHASE-TRANSFER GLYCOSYLATION; PYRAZOLES; PYRAZOLO[3,4-D]PYRIMIDINE; RIBONUCLEOSIDES
Erscheinungsdatum: 1992
Herausgeber: VCH PUBLISHERS INC
Journal: LIEBIGS ANNALEN DER CHEMIE
Ausgabe: 11
Startseite: 1165
Seitenende: 1170
Zusammenfassung: 
The synthesis of the 3- and 4-(methylthio)pyrazolo[3,4-d]pyrimidine N1- and N-2'-deoxy-beta-D-ribonucleosides 2b, 15 is described. Anionic glycosylation of 5-amino-3-(methylthio)-4-pyrazolecarbonitrile (4) or 4-(methylthio)pyrazolo[3,4-dipyrimidine (12) with 2-deoxy-3,5-di-O-(4-methylbenzoyl)-alpha-D-erythro-pentoturanosyl 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 alpha-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.
ISSN: 01702041

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