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https://doi.org/10.5562/cca2531

Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

Nataša Župančić ; TAPI Research and Development, PLIVA Croatia Ltd., Prilaz baruna Filipovića 25, 10 000 Zagreb, Croatia
Željka Ban ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Josipa Matić   ORCID icon orcid.org/0000-0003-1774-0446 ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Dijana Saftić   ORCID icon orcid.org/0000-0002-0657-1635 ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Ljubica Glavaš-Obrovac ; Department of Clinical Chemistry, Biochemistry and Clinical Chemistry, Faculty of Medicine, J. J. Strossmayer University of Osijek, Huttlerova 4,31000 Osijek, Croatia
Biserka Žinić   ORCID icon orcid.org/0000-0002-1536-7142 ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

Puni tekst: engleski, pdf (1 MB) str. 43-52 preuzimanja: 933* citiraj
APA 6th Edition
Župančić, N., Ban, Ž., Matić, J., Saftić, D., Glavaš-Obrovac, Lj. i Žinić, B. (2015). Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides. Croatica Chemica Acta, 88 (1), 43-52. https://doi.org/10.5562/cca2531
MLA 8th Edition
Župančić, Nataša, et al. "Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides." Croatica Chemica Acta, vol. 88, br. 1, 2015, str. 43-52. https://doi.org/10.5562/cca2531. Citirano 09.08.2020.
Chicago 17th Edition
Župančić, Nataša, Željka Ban, Josipa Matić, Dijana Saftić, Ljubica Glavaš-Obrovac i Biserka Žinić. "Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides." Croatica Chemica Acta 88, br. 1 (2015): 43-52. https://doi.org/10.5562/cca2531
Harvard
Župančić, N., et al. (2015). 'Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides', Croatica Chemica Acta, 88(1), str. 43-52. https://doi.org/10.5562/cca2531
Vancouver
Župančić N, Ban Ž, Matić J, Saftić D, Glavaš-Obrovac Lj, Žinić B. Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides. Croatica Chemica Acta [Internet]. 2015 [pristupljeno 09.08.2020.];88(1):43-52. https://doi.org/10.5562/cca2531
IEEE
N. Župančić, Ž. Ban, J. Matić, D. Saftić, Lj. Glavaš-Obrovac i B. Žinić, "Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides", Croatica Chemica Acta, vol.88, br. 1, str. 43-52, 2015. [Online]. https://doi.org/10.5562/cca2531

Sažetak
An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is
described. N-1′-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine
bases with protected 5-tosyl ribose. Additionally, N-1′,N-3′-disubstituted reversed nucleosides were
isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of
5′-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5′-ethynyl derivative which was further
transformed into 5′-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides
was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358,
CaCo-2, and HT-29). 5′-Iodouracil derivative displayed moderate growth inhibition activity against human
colon carcinoma (CaCo-2) cells.

Ključne riječi
uracil; 5-halogenuracil; D-ribose; reversed nucleosides; antitumor activity

Hrčak ID: 139128

URI
https://hrcak.srce.hr/139128

Posjeta: 1.337 *