Synthesis and biological properties of the four optical isomers of 5-o- carboranyl-2',3'-didehydro-2',3'-dideoxyuridine

Article abstract of DOI:10.1080/07328319808004670

The four isomers of the 5-o-carboranyl-2',3'-didehydro-2',3'- dideoxyuridine (d4CU) were synthesized and their antiviral activity and cytotoxicity in normal and cancer human cells determined. Coupling of silylated 5-o-carboranyluracil with the protected D/L 2,3-dideoxy-2- phenylselenenylribosylacetates provided after oxidative elimination and deprotection, the desired compounds. The presence of the electron deficient 5-o-carboranyl moiety on uracil influenced the yield of the various isomers. In general, the compounds demonstrated weak anti-human immunodeficiency virus activity in primary human lymphocytes. No marked difference in the biological profile was noted for the various optical isomers, suggesting that the high lipophilicity of these nucleosides imparted by the carboranyl moiety overrides stereochemical considerations in the 2',3'-didehydro-2',3'- dideoxyaglycon moiety.

Full text of DOI:10.1080/07328319808004670

Nucleosides and Nucleotides
ISSN: 0732-8311 (Print) (Online) Journal homepage: http://www.tandfonline.com/loi/lncn19
Synthesis and Biological Properties of the
Four Optical Isomers of 5-o-Carboranyl-2′,3′-
didehydro-2′,3′-dideoxyuridine
Jean-Christophe G. Graciet , Junxing Shi & Raymond F. Schinazi
To cite this article: Jean-Christophe G. Graciet , Junxing Shi & Raymond F. Schinazi (1998)
Synthesis and Biological Properties of the Four Optical Isomers of 5-o-Carboranyl-2′,3′-
didehydro-2′,3′-dideoxyuridine, Nucleosides and Nucleotides, 17:4, 711-727, DOI:
10.1080/07328319808004670
To link to this article: http://dx.doi.org/10.1080/07328319808004670
Published online: 13 Feb 2011.
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Date: 16 May 2016, At: 14:11