Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition |
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| Authors: | Benoit Métayer Andrea Angeli Agnès Mingot Kévin Jouvin Gwilherm Evano |
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| Affiliation: | 1. IC2MP-UMR CNRS 7582, Superacid Group–Organic Synthesis Team, Université de Poitiers, Poitiers, France;2. Department NEUROFARBA–Pharmaceutical and Nutraceutical Chemistry Section, Università degli Studi di Firenze, Sesto Fiorentino, Florence, Italy;3. Institut Lavoisier de Versailles, UMR CNRS 8180, Universitée de Versailles Saint-Quentin-en-Yvelines, Versailles, France;4. Laboratoire de Chimie Organique, Service de Chimie et Physico Chimie Organiques, Université Libre de Bruxelles, Brussels, Belgium |
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| Abstract: | After hydrofluorination of ynesulphonamides in superacid or in the presence of hydrofluoric acid/base reagents, a series of α-fluoroenamides has been synthesised and tested for the inhibition of carbonic anhydrase (CA, EC 4.2.1.1) isoforms. This study reveals a new, highly selective family of cancer-related transmembrane human (h) CA IX/XII inhibitors. These original fluorinated ureido isosters do not inhibit the widespread cytosolic isoforms hCA I and II and selectively inhibit the transmembrane cancer-related hCA IX and XII, offering interesting new leads for future studies. |
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| Keywords: | Superacid hydrofluorination fluorinated isosters carbonic anhydrase inhibitors ureas |
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