Development of a general and regioselective N-alkylation strategy of azoles and synthesis of original imidazole derivatives of chemical and biological interest
(2013)
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- Authors
- Supervisors
- Robiette, Raphaël
- Abstract
- Imidazoles are key structures in medicinal chemistry. Numbers of imidazole derivatives have found applications in the treatment of infectious diseases, cancer, metabolic, cardiovascular, and CNS disorders as well as analgesic and inflammatory conditions. One objective of our work is the synthesis and biological evaluation of a new family of macrocycles containing a 5-aryl-1H-imidazole motif. We found that our compounds possess cytostatic effects against cancers cells, including cell-lineages which are resistant to pro-apoptotic stimuli. The large panel of synthesized compounds allowed drawing some conclusions concerning the structure-activity relationship. We also investigated the chiral properties of macrocycles and showed that due to their cyclophane-type structure, depending on the ring size, some of these compounds are planar chiral molecules. In a second part, we have developed a regioselective N-alkylation of azoles providing the more sterically hindered isomer. Our methodology consists in a three-step one-pot process: protection of the parent azole, regioselective N-alkylation and finally deprotection.
- Affiliations
Citations
Van Den Berge, E. (2013). Development of a general and regioselective N-alkylation strategy of azoles and synthesis of original imidazole derivatives of chemical and biological interest. https://hdl.handle.net/2078.5/27140