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
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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 | ||||||||
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| 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 |
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| Divisions: | Division of Organic Chemistry and Biochemistry | ||||||||
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| Depositing User: | Dijana Pavlović Saftić | ||||||||
| Date Deposited: | 02 May 2018 13:08 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/4020 | ||||||||
| DOI: | 10.5562/cca2531 |
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