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. 2009 May;28(5):633-41.
doi: 10.1080/15257770903091920.

Carbocyclic thymidine analogues for use as potential therapeutic agents

Katherine L Seley-Radtke  1 , Naresh K Sunkara
Affiliations

Carbocyclic thymidine analogues for use as potential therapeutic agents

Katherine L Seley-Radtke et al. Nucleosides Nucleotides Nucleic Acids. 2009 May.

Abstract

The discovery of azidothymidine's (AZT) activity against human immunodeficiency virus (HIV) provided strong rationale for the design of additional thymidine analogues. One drawback of many nucleoside analogues is the toxicity that often arises due to phosphorylation by cellular kinases. In order to overcome this problem, a number of truncated nucleosides lacking the 4'-hydroxymethyl group have been synthesized. In that regard, the synthesis and preliminary biological results for two truncated carbocyclic thymidine analogues are presented herein.

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Figures

FIGURE 1
FIGURE 1
Biologically significant pyrimidine nucleosides.
FIGURE 2
FIGURE 2
Truncated purine carbocyclic nucleosides.
FIGURE 3
FIGURE 3
Proposed truncated thymidine carbocyclic targets.
SCHEME 1
SCHEME 1
Synthesis of 5 and 6. Reagents and conditions: a, CeCl3 • 7H2O NaBH4, MeOH, 0°C; b, i) PPh3, DIAD, CH3CN, 0°C to rt, 24 h; c, NaOH, MeOH, 12 h; d, TFA:H2O (2:1), 1 h, rt; e, 10% Pd/C, H2, 25 psi, 25 min, rt.
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