Synthesis and antiviral activity of boranophosphonate isosteres of AZT and d4T monophosphates.

Authors :: Barral K
Priet S
De Michelis C
Sire J
Neyts J
Balzarini J
Canard B
Alvarez K
Source :: European journal of medicinal chemistry [Eur J Med Chem] 2010 Feb; Vol. 45 (2), pp. 849-56. Date of Electronic Publication: 2009 Nov 12.
Publication Year :: 2010
Abstract: We report synthesis, in vitro antiviral activity, and stability studies in biological media of original boranophosphonate isosteres of AZT and d4T monophophates. A convenient route for the synthesis of 3'-Azido-3'-deoxythymidine-5'-boranophosphonate 8 and 2',3'-Didehydro-3'-dideoxythymidine-5'-boranophosphonate 12 is described. H-phosphinates 7 and 11, and alpha-boranophosphonates 8 and 12 exhibited no significant in vitro activity against HIV-infected cells, neither against a broad panel of viruses, up to 200 microM. The absence of activity of target compounds 8 and 12 can be partially explained by their short half-life in culture medium.<br /> (Copyright 2009 Elsevier Masson SAS. All rights reserved.)

Subjects :: Animals
Antiviral Agents chemistry
Antiviral Agents metabolism
Cell Line
Drug Stability
Half-Life
Humans
Organophosphonates chemistry
Organophosphonates metabolism
Viruses drug effects
Antiviral Agents chemical synthesis
Antiviral Agents pharmacology
Organophosphonates chemical synthesis
Organophosphonates pharmacology
Stavudine analogs & derivatives
Zidovudine analogs & derivatives

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