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Modifications at the C(5) position of pyrimidine nucleosides

Witold Kozak 1
Witold Kozak
, 
Sebastian Demkowicz 2
Sebastian Demkowicz
, 
Mateusz Daśko 3
Mateusz Daśko
, 
Janusz Rachoń 2
Janusz Rachoń
, 
Janusz Rak 1
Janusz Rak
1 University of Gdańsk, Faculty of Chemistry, Laboratory of Biological Sensitizers, Poland
2 Gdańsk University of Technology, Faculty of Chemistry, Department of Organic Chemistry, Poland
3 Gdańsk University of Technology, Faculty of Chemistry, Department of Inorganic Chemistry, Poland
10.1070/RCR4919
Published 30 November 2019
Review , RCR4919, Volume 89, Issue 3, 281-310
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Kozak W. et al. Modifications at the C(5) position of pyrimidine nucleosides // Russian Chemical Reviews. 2019. Vol. 89. No. 3. pp. 281-310.
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Kozak W., Demkowicz S., Daśko M., Rachoń J., Rak J. Modifications at the C(5) position of pyrimidine nucleosides // Russian Chemical Reviews. 2019. Vol. 89. No. 3. pp. 281-310.
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TY - JOUR
DO - 10.1070/RCR4919
UR - https://rcr.colab.ws/publications/10.1070/RCR4919
TI - Modifications at the C(5) position of pyrimidine nucleosides
T2 - Russian Chemical Reviews
AU - Kozak, Witold
AU - Demkowicz, Sebastian
AU - Daśko, Mateusz
AU - Rachoń, Janusz
AU - Rak, Janusz
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 281-310
IS - 3
VL - 89
ER -
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@article{2019_Kozak,
author = {Witold Kozak and Sebastian Demkowicz and Mateusz Daśko and Janusz Rachoń and Janusz Rak},
title = {Modifications at the C(5) position of pyrimidine nucleosides},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4919},
number = {3},
pages = {281--310},
doi = {10.1070/RCR4919}
}
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Kozak, Witold, et al. “Modifications at the C(5) position of pyrimidine nucleosides.” Russian Chemical Reviews, vol. 89, no. 3, Nov. 2019, pp. 281-310. https://rcr.colab.ws/publications/10.1070/RCR4919.
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Abstract

This review summarizes the state of knowledge on the chemical methods of C(5)-modifications of uridine and cytidine derivatives and may serve as a useful tool for synthetic chemists to choose an appropriate reaction protocol. The synthesis of 5-substituted uracil derivatives is gaining an increasing interest because of their possible applications in medicine and pharmacy. Modifications at the C(5) position of pyrimidine nucleosides can enhance their biostability, bioavailability or(and) biological activity. Among the C(5)-modified nucleosides, 5-halopyrimidines exhibit anticancer, antiviral, radio- and photosensitizing properties. Besides 5-halo-substituted derivatives, there are other examples of nucleosides with confirmed biological activity containing a C--C bond at the C(5) position in the pyrimidine ring. In recent decades, scientists have achieved great progress in the field of cross-coupling reactions. Among them, nickel-catalyzed processes provide a broad spectrum of synthetic methods that are based on less toxic and cheaper starting materials. This review summarizes the synthetic approaches based on the coupling or halogenation reactions, which enable 5-substituted pyrimidine nucleosides to be obtained. Moreover, the importance of the systems considered for medicine and pharmacy is briefly discussed.

Bibliography --- 197 references.

Funders

National Science Centre (Narodowe Centrum Nauki)
2014/14/A/ST4/00405

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