Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 28, Issue 10, Pages 1931-1936Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2018.03.063
Keywords
Nucleoside analogues; Modular syntheses; Green chemistry; Anti-CML agents
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Funding
- PHC Toubkal
- UCA
- CNRS
- CNRST
- Institut National du Cancer [INCa-PRTK2012-045]
- Canceropole PACA
- COST [CA15135]
- Fondation ARC pour la Recherche Contre le Cancer [PGA1RF20170205389]
- Association Laurette Fugain Grant [2014-04]
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The C-aryl-ribosyles are of utmost interest for the development of antiviral and anticancer agents. Even if several synthetic pathways have been disclosed for the preparation of these nucleosides, a direct, few steps and modular approaches are still lacking. In line with our previous efforts, we report herein a one step - eco-friendly beta-ribosylation of aryles and heteroaryles through a direct Friedel-Craft ribosylation mediated by bismuth triflate, Bi(OTf)(3). The resulting carbohydrates have been functionalized by cross-coupling reactions, leading to a series of new C-aryl-nucleosides (32 compounds). Among them, we observed that 5d exerts promising anti-proliferative effects against two human Chronic Myeloid Leukemia (CML) cell lines, both sensitive (K562-S) or resistant (K562-R) to imatinib, the gold standard of care used in this pathology. Moreover, we demonstrated that 5d kills CML cells by a non-conventional mechanism of cell death. (C) 2018 Published by Elsevier Ltd.
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