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Synthesis and biological activity of reversed pyrimidine nucleosides

By Nataša Župančić, Željka Ban, Josipa Matić, Dijana Saftić, Ljubica Glavaš-Obrovac and Biserka Žinić

Abstract

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

Topics: Chemistry
Publisher: Croatian Chemical Society
Year: 2015
DOI identifier: 10.5562/cca2531
OAI identifier: oai:fulir.irb.hr:2823

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