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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 id orcid.org/0000-0003-1774-0446 ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Dijana Saftić orcid id 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 id 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 1.254 Kb

str. 43-52

preuzimanja: 1.273

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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: 1.957 *