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Synthesis and biological activity of reversed pyrimidine nucleosides

Župančić, Nataša; Ban, Željka; Matić, Josipa; Saftić, Dijana; Glavaš-Obrovac, Ljubica; Žinić, Biserka (2015) Synthesis and biological activity of reversed pyrimidine nucleosides. Croatica Chemica Acta, 88 (1). pp. 43-52. ISSN 0011-1643

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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.

Item Type: Article
Uncontrolled Keywords: uracil; 5-halogenuracil; D-ribose; reversed nucleosides; antitumor activity
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Synthesis of novel biologically active nucleobase and nucleotide derivatives (Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida)-Biserka Žinić098-0982914-2935MZOS
Depositing User: Željka Ban
Date Deposited: 31 May 2016 10:22
DOI: 10.5562/cca2531

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