hrvatski jezikClear Cookie - decide language by browser settings

Synthesis and biological activity of reversed pyrimidine nucleosides

Župančić, Nataša; Ban, Željka; Matić, Josipa; Saftić, Dijana; Glavaš-Obrovac, Ljubica; Žinić, Biserka (2014) Synthesis and biological activity of reversed pyrimidine nucleosides. Croatica Chemica Acta, 88 (1). pp. 43-52. ISSN 0011-1643

[img]
Preview
PDF - Published Version - article
Available under License Creative Commons Attribution.

Download (399kB) | Preview

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.

Item Type: Article
Additional Information: This work was supported by the Ministry of Science, Education and Sports of the Republic of Croatia through Grant No. 098-0982914-2935
Uncontrolled Keywords: uracil; 5-halogenuracil; D-ribose; reversed nucleosides; antitumor activity
Subjects: NATURAL SCIENCES
NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
NATURAL SCIENCES > Biology
NATURAL SCIENCES > Biology > Microbiology
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida-Biserka Žinić098-0982914-2935MZOS
Depositing User: Dijana Saftić
Date Deposited: 02 May 2018 13:08
Last Modified: 02 May 2018 13:08
URI: http://fulir.irb.hr/id/eprint/4020
DOI: 10.5562/cca2531

Actions (login required)

View Item View Item

Downloads

Downloads per month over past year