Title: Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides
Authors: El Akri, Khalid ×
Bougrin, Khalid
Balzarini, Jan
Faraj, Abdesslem
Benhida, Rachid #
Issue Date: Dec-2007
Publisher: Pergamon Press
Series Title: Bioorganic & Medicinal Chemistry Letters vol:17 issue:23 pages:6656-6659
Abstract: We report herein an efficient synthesis of 4-substituted triazolyl-nucleosides and their in vitro cytostatic activity. The synthesis is based on a straightforward 1,3-dipolar cycloaddition between 1-azido-ribose 2 and terminal alkynes under a cooperative effect of microwave activation and copper (I) catalysis. All cycloadducts were obtained in nearly quantitative yield after a short reaction time (1 to 2min). After removal of acetyl protecting groups, the free nucleosides were evaluated against L1210, Molt4/C8, and CEM tumor cell lines. Structure-activity relationship study shows that the substituent on the triazole ring has a major effect since nucleosides 4c and 4g, containing, respectively, a long alkyl chain and an aryl donor group are the most active compounds in this series.
ISSN: 0960-894X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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