Abstract:
:Synthesis of the 4'-ethynyl and 4'-cyano phosphonates 8-11, which mimic the 5'-monophosphate of 4'-branched 2',3'-didehydro-2',3'-dideoxy nucleosides, was investigated by employing the 3',4'-unsaturated nucleosides (13 and 28) as the starting material. The synthesis was initiated by the electrophilic addition of NIS/(EtO)(2)P(O)CH(2)OH to these unsaturated nucleosides. After introduction of the 2',3'-double bond, the 4'-hydroxylmethyl group of the resulting adducts was transformed into the ethynyl or cyano group. While the 4'-cyano phosphonates 9 and 11 were not sufficiently stable to be isolated, the 4'-ethynyl counterparts (8 and 10) were obtained as their mono-ammonium salts. The adenine derivative 8 showed almost comparable anti-HIV-1 activity to that of d4T.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Kubota Y,Ishizaki N,Haraguchi K,Hamasaki T,Baba M,Tanaka Hdoi
10.1016/j.bmc.2010.08.037subject
Has Abstractpub_date
2010-10-15 00:00:00pages
7186-92issue
20eissn
0968-0896issn
1464-3391pii
S0968-0896(10)00782-0journal_volume
18pub_type
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