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Synthesis and Biological Activity of 2′‐Fluoro‐ D ‐arabinofuranosylpyrazolo[3,4‐ d ]pyrimidine Nucleosides
Author(s) -
ShortnacyFowler Anita T.,
Tiwari Kamal N.,
Montgomery John A.,
Buckheit, Jr. Robert W.,
Secrist III John A.,
Seela Frank
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19991215)82:12<2240::aid-hlca2240>3.0.co;2-2
Subject(s) - chemistry , anomer , pyrimidine , nucleoside , adenosine deaminase , yield (engineering) , derivative (finance) , stereochemistry , human cytomegalovirus , bromide , adenosine , biochemistry , organic chemistry , materials science , financial economics , economics , metallurgy , gene
Coupling of 2‐fluoro‐3,5‐di‐ O ‐benzoyl‐ α ‐ D ‐arabinofuranosyl bromide with 4‐methoxypyrazolo[3,4‐ d ]pyrimidine gave an α ‐ D / β ‐ D mixture of N 1 ‐ and N 2 ‐coupled products. All the anomers were separated and deblocked to yield the corresponding nucleosides. The β ‐ D ‐anomer 7 was converted to the 4‐amino derivative 11 , which was deaminated by adenosine deaminase to give the 4‐oxo compound 12 . Compound 7 showed significant activity against human cytomegalovirus and hepatitis B virus, and compound 11 showed activity against human herpes virus 8. All the compounds were noncytotoxic in several human tumor‐cell lines in culture.