Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides |
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| Authors: | El Akri Khalid Bougrin Khalid Balzarini Jan Faraj Abdesslem Benhida Rachid |
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| Affiliation: | 1. Laboratoire de Chimie des Molécules Bioactives et des Arômes, UMR-CNRS 6001, Institut de Chimie de Nice, Université de Nice-Sophia Antipolis, Parc Valrose, F-06108 Nice Cédex 2, France;2. Laboratoire de Chimie des Plantes et de Synthèse organique et Bioorganique, Université Mohammed V-Agdal, Faculté des Sciences B.P., 1014 Rabat, Morocco;3. Rega Institute for Medical Research, Katholieke Univesiteit Leuven, Minderbroedersstraat 10, BE-3000 Leuven, Belgium;4. Theravia, EFS, 240 Avenue E. Jeanbrau, 34095 Montpellier, France |
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| 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. |
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