Naslov
Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

Autori
Župančić, Nataša ; Ban, Željka ; Matić, Josipa ; Saftić, Dijana ; Glavaš-Obrovac, Ljubica ; Žinić, Biserka

Izvornik
Croatica chemica acta (0011-1643) 88 (2015), 1; 43-52

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA