Synthesis of Novel Thymine-β-lactam Hybrids and Evaluation of Their Antitumor Activity

Abstract Trimethylene-tethered thymine-β-lactam and thymine-bis-β-lactam chimeras were prepared as novel classes of hybrid systems through selective mono- or bis-N-alkylation of thymine with cis -1-(3-bromopropyl)-β-lactams. In addition, acidic methanolysis of the β-lactam nucleus in these systems p...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2014-09, Vol.46 (18), p.2436-2444
Main Authors: Piens, Nicola, De Vreese, Rob, De Neve, Nympha, Van Hecke, Kristof, Balzarini, Jan, De Kimpe, Norbert, D’hooghe, Matthias
Format: Article
Language:English
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Summary:Abstract Trimethylene-tethered thymine-β-lactam and thymine-bis-β-lactam chimeras were prepared as novel classes of hybrid systems through selective mono- or bis-N-alkylation of thymine with cis -1-(3-bromopropyl)-β-lactams. In addition, acidic methanolysis of the β-lactam nucleus in these systems provided an entry into the class of thymine-β-amino ester hybrids. A selection of the newly synthesized hybrid compounds was assessed for their antiviral activity, cytotoxicity, and cytostatic activity, revealing a significant cytostatic effect of one of the derivatives against murine leukemia and human T-lymphocyte tumor cells.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1338647