https://orcid.org/0000-0003-1647-4262
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Abstract
A one-pot two-step protocol was developed for the synthesis of a series of novel 4-cyanamidobenzenesulfonamides from easily accessible methyl (4-sulfamoylphenyl)-carbamimidothioate. The new sulphonamides were investigated as inhibitors of the enzyme carbonic anhydrase (CA, EC 4.2.1.1), the human (h) cytosolic isoforms hCA I, II, VII, and XIII, as well as three bacterial enzymes belonging to the β-CA class, MscCA from Mammaliicoccus (Staphylococcus) sciuri and StCA1 and StCA2, from Salmonella enterica (serovar Typhimurium). The human isoforms were generally effectively inhibited by these compounds, with a clear structure-activity relationship privileging long aliphatic chains (C6, C7 and C18) as substituents at the cyanamide functionality. The bacterial CAs were also inhibited by these compounds, but not as effective as the hCAs. The most sensitive enzyme to these inhibitors was StCA1 (KIs of 50.7 − 91.1 nM) whereas SscCA was inhibited in the micromolar range (KIs of 0.86–9.59 µM).
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Disclosure statement
No potential conflict of interest was reported by all author(s) except CTS. CT Supuran is Editor-in-Chief of the Journal of Enzyme Inhibition and Medicinal Chemistry. He was not involved in the assessment, peer review, or decision-making process of this paper. The authors have no relevant affiliations of financial involvement with any organisation or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.