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Synthesis and Anti‐HIV Activity of 5‐Alkoxymethyl‐3′‐azido‐2′,3′‐dideoxyuridines
Author(s) -
AbdelMegied Ahmed E.S.,
Hansen Poul,
Pedersen Erik B.,
Nielsen Claus,
Nielsen Carsten M.
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260702
Subject(s) - anomer , chemistry , human immunodeficiency virus (hiv) , biological activity , alkyl , stereochemistry , chemical synthesis , diastereomer , combinatorial chemistry , organic chemistry , biochemistry , biology , in vitro , virology
Methyl 3‐azido‐5‐ O‐tert ‐butyldiphenylsilyl‐2,3‐dideoxy‐D‐ erythro ‐furanoside ( 3 ) was coupled with silylated 5‐hydroxymethyluracil ( 1a ) and its C 1 ‐C 6 alkyl ethers 1b – g to give the corresponding protected nucleosides 4a ‐ g which were deprotected with Bu 4 NF to afford 3‐azido nucleosides 5a ‐ g and 6a ‐ g . The α‐anomers 6f , g show moderate activity against HIV. No significant activity against HSV‐1 was found for the compounds 5 and 6 .
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