{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T18:41:32Z","timestamp":1787510492172,"version":"build-2736575974"},"reference-count":44,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2024,7,30]],"date-time":"2024-07-30T00:00:00Z","timestamp":1722297600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2024,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    We synthesized herein 16 compounds (\n                    <jats:bold>SUT1<\/jats:bold>\n                    \u2013\n                    <jats:bold>SUT16<\/jats:bold>\n                    ) as potential carbonic anhydrase (CA) inhibitors utilizing the tail\u2010approach design. Based on this strategy, we connected benzenesulfonamide, the zinc\u2010binding scaffold, to different urea moieties with the 1,3,4\u2010thiadiazole ring as a linker. We obtained the target compounds by the reaction of 4\u2010(5\u2010amino\u20101,3,4\u2010thiadiazol\u20102\u2010yl)benzenesulfonamide with aryl isocyanates. Upon confirmation of their structures, the compounds were screened for their ability to inhibit the tumor\u2010related human (h) isoforms human carbonic anhydrase (hCA) IX and XII, as well as the physiologically dominant hCA I and II. Most of the molecules demonstrated\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>i<\/jats:sub>\n                    values\u2009\u2264\u200910\u2009nM with different selectivity profiles. The binding modes of\n                    <jats:bold>SUT9<\/jats:bold>\n                    ,\n                    <jats:bold>SUT10<\/jats:bold>\n                    , and\n                    <jats:bold>SUT5<\/jats:bold>\n                    , the most effective inhibitors of hCA II, IX, and XII, respectively, were predicted by molecular docking.\n                    <jats:bold>SUT16<\/jats:bold>\n                    (4\u2010{5\u2010[3\u2010(naphthalen\u20101\u2010yl)ureido]\u20101,3,4\u2010thiadiazol\u20102\u2010yl}benzenesulfonamide) was found to be the most selective inhibitor of the cancer\u2010associated isoforms hCA IX and XII over the off\u2010target isoforms, hCAI and II. The interaction dynamics and stability of\n                    <jats:bold>SUT16<\/jats:bold>\n                    within hCA IX and XII were investigated by molecular dynamics simulations as well as dynophore analysis. Based on computational data, increased hydrophobic contacts and hydrogen bonds in the tail part of these molecules within hCA IX and XII were found as favorable interactions leading to effective inhibitors of cancer\u2010related isoforms.\n                  <\/jats:p>","DOI":"10.1002\/ardp.202400439","type":"journal-article","created":{"date-parts":[[2024,7,30]],"date-time":"2024-07-30T22:45:26Z","timestamp":1722379526000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Tail\u2010approach based design, synthesis, and molecular modeling of benzenesulfonamides carrying thiadiazole and urea moieties as novel carbonic anhydrase inhibitors"],"prefix":"10.1002","volume":"357","author":[{"given":"M. \u0130hsan","family":"Han","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Erciyes University Kayseri 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Dilem","family":"Do\u011fan","sequence":"additional","affiliation":[{"name":"Department of Basic Sciences, Faculty of Pharmacy Erciyes University Kayseri 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