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Review
. 2015 Mar 18;20(3):4967-97.
doi: 10.3390/molecules20034967.

Synthesis of C-arylnucleoside analogues

Christophe Len  1   2 , Gérald Enderlin  3
Affiliations
Review

Synthesis of C-arylnucleoside analogues

Christophe Len et al. Molecules. .

Abstract

Modified nucleoside analogues are of great biological importance as antiviral and antitumoral agents. There is special interest in the preparation of C-aryl nucleosides with an aromatic ring in different positions of the glycone for their biological activity. Different chemical synthesis strategies for these targets are described in this review.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of 3'(S)-C-phenyl-β-D-xylofuranosyluracil (4).
Scheme 2
Scheme 2
Synthesis of 5'(S)- and 5'(R)-C-phenyluridine analogues 11 and 12.
Scheme 3
Scheme 3
Synthesis of 1-C-phenyl-D-ribofuranosyl analogues 15.
Scheme 4
Scheme 4
Synthesis of thymidine analogues 23 and 24.
Figure 1
Figure 1
Bicyclo[3.3.0]octane nucleoside analogues 25–40 having a phenyl group [13,14,15].
Figure 2
Figure 2
Bicyclo[3.3.0]octane nucleoside analogues 41–50 having a substituted aromatic ring.
Scheme 5
Scheme 5
Synthesis of 1'(R)- and 1'(S)-C-phenyl-D-ribofuranosylthymine analogues 53 and 54.
Figure 3
Figure 3
1'(R)- and 1'(S)-C-phenyl-D-ribofuranosylnucleoside analogues 55–62.
Scheme 6
Scheme 6
Synthesis of (4'(R)-C-phenyl-D-ribo-tetrofuranosyl)adenine analogue 69.
Scheme 7
Scheme 7
Synthesis of (4'(R)-C-phenyl-D-ribotetrofuranosyl)adenine analogue 74.
Scheme 8
Scheme 8
Synthesis of 5(R)-C-phenyltetrahydrofurane derivative 81.
Figure 4
Figure 4
5(R)-(4-Fluorophenyl)tetrahydrofuran derivative 82.
Scheme 9
Scheme 9
Synthesis of 3'(S)-C-phenyl-β-D-xylofuranosyluracil (4).
Scheme 10
Scheme 10
Synthesis of 2'(S)-C-phenyl-β-D-arabinofuranosyluracil (84).
Scheme 11
Scheme 11
Synthesis of (2(R)-C-phenylribofuranosyl)thymine derivative 94.
Figure 5
Figure 5
(2(R)-C-Phenylribofuranosyl)cytosine derivative 95.
Scheme 12
Scheme 12
Synthesis of 3'-C-phenyl d4U analogue 104.
Scheme 13
Scheme 13
Synthesis of 3'-C-phenyl d4A analogue 113.
Scheme 14
Scheme 14
Synthesis of 2'-C-phenyl d4U analogue 121.
Scheme 15
Scheme 15
Synthesis of 3'-C-phenyl d4T 126.
Figure 6
Figure 6
3'-C-Aryl d4U 127–132 and 3'-C-aryl d4C 133–137.
Scheme 16
Scheme 16
Synthesis of 3'(S)-C-phenyl ddC analogue 141.
Figure 7
Figure 7
3'(S)-C-aryl ddC 142–144.
Scheme 17
Scheme 17
Synthesis of 1'(R)-C-phenyl uridine analogue 147.
Scheme 18
Scheme 18
Possible reaction pathway for the synthesis of 1'(R)-C-phenyl uridine analogue 147.
Scheme 19
Scheme 19
Synthesis of isochroman derivative 154.
Figure 8
Figure 8
Isochroman derivatives 155 and 156.
Scheme 20
Scheme 20
Synthesis of the 3'-C-spiro uridine analogue 165.
Figure 9
Figure 9
3'-C-Spiro uridine analogues 166–177.
Scheme 21
Scheme 21
Synthesis of the 4'-C-phenyl thimidine analogues 189 and 190.
Figure 10
Figure 10
4'-C-Phenyl thimidine analogues 191–194.
Scheme 22
Scheme 22
Synthesis of the 4'-C-phenyl L-uridine analogues 203 and 204.
Figure 11
Figure 11
4'-C-Phenyl purine analogue 205.
Scheme 23
Scheme 23
Synthesis of the benzo[c]furan analogues of d4U 214 and 215.
Figure 12
Figure 12
Benzo[c]furan nucleoside analogues 216–220.
See this image and copyright information in PMC

References

    1. Len C., Mackenzie G. Synthesis of 2',3'-didehydro-2',3'-dideoxynucleosides having variations at either or both of the 2'- and 3'-positions. Tetrahedron. 2006;62:9085–9107. doi: 10.1016/j.tet.2006.07.050. - DOI
    1. Len C., Postel D. Synthesis of 2',3'-didehydro-2',3'-dideoxynucleosides via nucleoside route. Curr. Org. Synth. 2006;21:261–281. doi: 10.2174/157017906777934881. - DOI
    1. Lebreton J., Escudier J.M., Arzel L., Len C. Synthesis of bicyclonucleosides having a C-C bridge. Chem. Rev. 2010;110:3371–3418. doi: 10.1021/cr800465j. - DOI - PubMed
    1. Len C., Mondon M., Lebreton J. Synthesis of cyclonucleosides having a C-C bridge. Tetrahedron. 2008;64:7453–7475. doi: 10.1016/j.tet.2008.04.095. - DOI
    1. Herve G., Sartori G., Enderlin G., Mackenzie G., Len C. Palladium-catalysed Suzuki reaction in aqueous solvents applied to unprotected nucleosides and nucleotides. RSC Adv. 2014;4:18558–18594. doi: 10.1039/c3ra47911k. - DOI

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