Journal
TETRAHEDRON LETTERS
Volume 57, Issue 7, Pages 743-746Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.01.006
Keywords
6,5 '-O-Anhydrouridines; Oxazolopyrimidines; Dioxazepine rearrangement; Ring contraction; Cytotoxicity
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Funding
- Polish Ministry of Science and Higher Education [IP2010 026070]
- Centre for Preclinical Research and Technology (CePT)
- European Regional Development Fund and Innovative Economy
- National Cohesion Strategy of Poland
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We report a mild and efficient approach to the optically pure 6H-oxazolo[3,2-f]pyrimidine-5,7-dione scaffold via the unexpected rearrangement and ring contraction of 2,3-dihydropyrimido[6,1-b][1,5,3]-dioxazepine-7,9(5H,8H)-diones derived from nucleoside precursors. The developed procedure enables the synthesis of a wide range of compounds with great structural diversity. The structure of the obtained compounds was confirmed by NMR spectroscopy and single crystal X-ray structural analysis. The final products were tested for cytotoxic effect on one non-cancerous (fibroblasts) and six cancer cell lines of different origins (colon, glioma, breast, cervix, vulvar, and lung). The synthesized products are low molecular weight compounds with lead-like properties suitable for a medicinal chemistry optimization program. (C) 2016 Elsevier Ltd. All rights reserved.
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