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The need of selective inhibitors and the involvement of these metalloenzymes in many multifaceted diseases boost the search for new ligands able to distinguish among the different CA isoforms, and for multifunctional systems simultaneously able to inhibit CAs and to interfere with other pathological events by interacting with additional targets. In this work, we successfully explored the possibility of preparing new CAs ligands by combining calixarenes with benzensulfonamide units. Inhibition tests towards three human CA isoforms evidenced, for some of the ligands, K<jats:sub>i<\/jats:sub> values in the nanomolar range and promising selectivity. X\u2010ray and molecular modeling studies provided information on the mode of binding of these calixarene derivatives. 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