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The ability of boronic acid moieties to bind zinc ions was first hypothesized by the inhibitory activity of bortezomib, a boron\u2010containing protease inhibitor, on different isoforms of the Carbonic Anhydrase (CA, EC: 4.2.1.1) enzyme family and then assessed through X\u2010ray crystallographic studies on benzoxaboroles in complex with hCA II. These findings, along with the overexpression of isoforms IX and XII in hypoxic cancer and, in particular, breast cancer, drove us to explore the chemical space around the phenylboronic acids by generating a focused library of 16 derivatives (1\u20134a\u2013d) decorated with alkyl sulfonyl hydrazones. The compounds were then subjected to stopped flow\u2010based inhibition assays on a panel of hCAs, including the tumor\u2010associated isoforms, revealing low micromolar inhibition constants (<jats:italic>K<\/jats:italic><jats:sub>I<\/jats:sub>s) in some cases. 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