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Synthesis and Properties of Methylthiopyrazolo[3,4‐ d ]pyrimidine 2′‐Deoxy‐β‐ D ‐ribonucleosides
Author(s) -
Oertel Frank,
Winter Holger,
Kazimierczuk Zygmunt,
Vilpo J. A.,
Richter Peter,
Seela Frank
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201191
Subject(s) - chemistry , pyrimidine , deamination , glycosylation , deoxyribonucleosides , stereochemistry , adenosine deaminase , ribonucleoside , nucleic acid , adenosine , biochemistry , dna , enzyme , rna , gene
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.