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Synthesis and Antiviral Evaluation of Carbocyclic 3′‐Azidothymidine (AZT) Analogues and Their cyclo Sal‐Phosphate Triesters
Author(s) -
Ludek Olaf R.,
Balzarini Jan,
Meier Chris
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500719
Subject(s) - chemistry , zidovudine , nucleoside , phosphate , in vitro , stereochemistry , nucleoside analogue , human immunodeficiency virus (hiv) , organic chemistry , biochemistry , virology , viral disease , biology
Carbocyclic analogues of the anti ‐HIV dideoxynucleoside 3′‐azido‐3′‐deoxythymidine AZT ( 1 ) were synthesized. Starting from the enantiomerically pure carbocyclic 2′‐deoxythymidine 2 , four different carbocyclic AZT analogues 2 , 4 – 6 were prepared. Moreover, the nucleoside analogues were converted into their membrane‐permeable cyclo Sal‐phosphate triesters. All compounds were tested in vitro for their anti ‐HIV activity in human T‐lymphocytes (CEM/0). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)