{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T04:08:12Z","timestamp":1784779692526,"version":"3.55.0"},"reference-count":47,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,2,8]],"date-time":"2023-02-08T00:00:00Z","timestamp":1675814400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["1.1.1.2\/VIAA\/3\/19\/398"],"award-info":[{"award-number":["1.1.1.2\/VIAA\/3\/19\/398"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2023,3,14]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Two novel sulfaguanidine series, six <jats:italic>N<\/jats:italic>\u2010(<jats:italic>N<\/jats:italic>,<jats:italic>N\u2032<\/jats:italic>\u2010dialkyl\/dibenzyl\u2010carbamimidoyl) benzenesulfonamide derivatives and nine <jats:italic>N<\/jats:italic>\u2010(<jats:italic>N<\/jats:italic>\u2010alkyl\/benzyl\u2010carbamimidoyl) benzenesulfonamide derivatives, were obtained by desulfidative amination of easily accessible dimethyl arylsulfonylcarbonimidodithioates under catalyst\u2010 and base\u2010free conditions. The newly synthesized compounds were tested for the inhibition of four different isozymes of human carbonic anhydrase (hCA\u2005I, II, IX and XII, EC 4.2.1.1). Both series reported here were inactive against the off\u2010target isozymes hCA\u2005I and II (K<jats:sub>i<\/jats:sub>&gt;100\u2005\u03bcM). Interestingly, all investigated compounds inhibited both target isozymes hCA\u2005IX and XII in the submicromolar to micromolar ranges in which K<jats:sub>i<\/jats:sub> values spanned from 0.168 to 0.921\u2005\u03bcM against hCA\u2005IX and from 0.335 to 1.451\u2005\u03bcM against hCA\u2005XII. The results indicated that <jats:italic>N<\/jats:italic>\u2010(<jats:italic>N<\/jats:italic>\u2010alkyl\/benzyl\u2010carbamimidoyl) benzenesulfonamides were slightly more potent inhibitors than <jats:italic>N<\/jats:italic>\u2010(<jats:italic>N<\/jats:italic>,<jats:italic>N\u2032<\/jats:italic>\u2010dialkyl\/dibenzyl\u2010carbamimidoyl) benzenesulfonamides. Among the evaluated compounds, <jats:italic>N<\/jats:italic>\u2010<jats:italic>n<\/jats:italic>\u2010octyl\u2010substituted <jats:italic>N<\/jats:italic>\u2010carbamimidoylbenzenesulfonamide showed the most significant activity with a K<jats:sub>i<\/jats:sub> value of 0.168\u2005\u03bcM against hCA\u2005IX, which was four\u2010fold more selective toward this isozyme versus hCA\u2005XII. Again, another derivative from <jats:italic>N<\/jats:italic>\u2010(<jats:italic>N<\/jats:italic>\u2010alkyl\/benzyl\u2010carbamimidoyl) benzenesulfonamide series, <jats:italic>N<\/jats:italic>\u2010<jats:italic>p<\/jats:italic>\u2010methylbenzyl\u2010substituted <jats:italic>N<\/jats:italic>\u2010carbamimidoylbenzenesulfonamide, demonstrated superior inhibitory activity against hCA\u2005XII with a K<jats:sub>i<\/jats:sub> value of 0.335\u2005\u03bcM.<\/jats:p>","DOI":"10.1002\/cmdc.202200658","type":"journal-article","created":{"date-parts":[[2023,1,24]],"date-time":"2023-01-24T04:58:17Z","timestamp":1674536297000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Inhibition Studies on Carbonic Anhydrase Isoforms I, II, IX, and XII with a Series of Sulfaguanidines"],"prefix":"10.1002","volume":"18","author":[{"given":"Morteza","family":"Abdoli","sequence":"first","affiliation":[{"name":"Institute of Technology of Organic Chemistry Faculty of Materials Science and Applied Chemistry Riga Technical University  P. Valdena iela 3 1048 Riga Latvia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Viviana","family":"De Luca","sequence":"additional","affiliation":[{"name":"Department of Biology Agriculture and Food Sciences Institute of Biosciences and Bioresources  Via Pietro Castellino 111 80131 Napoli Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Clemente","family":"Capasso","sequence":"additional","affiliation":[{"name":"Department of Biology Agriculture and Food Sciences Institute of Biosciences and Bioresources  Via Pietro Castellino 111 80131 Napoli Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"NEUROFARBA Department Pharmaceutical and Nutraceutical Section University of Florence  Via Ugo Schiff 6 50019 Florence Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raivis","family":"\u017dalubovskis","sequence":"additional","affiliation":[{"name":"Institute of Technology of Organic Chemistry Faculty of Materials Science and Applied Chemistry Riga Technical University  P. Valdena iela 3 1048 Riga Latvia"},{"name":"Latvian Institute of Organic Synthesis  Aizkraukles 21 1006 Riga Latvia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,2,8]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11120-011-9635-3"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2021.1972995"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1042\/BCJ20160115"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2012.04.044"},{"key":"e_1_2_8_6_1","unstructured":"\u00a0"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.3390\/ijms231912045"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1077823"},{"key":"e_1_2_8_9_1","unstructured":"\u00a0"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1080\/13543784.2018.1548608"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1080\/13543784.2021.2014813"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.3390\/metabo8020025"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.3390\/cancers14143297"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.14.68"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1128426"},{"key":"e_1_2_8_18_1","unstructured":"\u00a0"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm500255y"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1235040"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2017.04.007"},{"key":"e_1_2_8_22_1","unstructured":"\u00a0"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2017.1356295"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.3390\/metabo8020037"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2022.2080816"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2022.2138367"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2022.2142787"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.3390\/ijms232214115"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.04.055"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm200466r"},{"key":"e_1_2_8_31_1","unstructured":"\u00a0"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.01.038"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.04.072"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)62326-9"},{"key":"e_1_2_8_35_1","unstructured":"\u00a0"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2017.1405264"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800941"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2020.1752201"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2018.1512597"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1155\/MBD.2001.137"},{"key":"e_1_2_8_41_1","unstructured":"\u00a0"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2017.04.007"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(97)86179-X"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2003.12.029"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.14.68"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.12.054"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.07.038"}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202200658","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cmdc.202200658","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202200658","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T08:46:45Z","timestamp":1760258805000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.202200658"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,8]]},"references-count":47,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2023,3,14]]}},"alternative-id":["10.1002\/cmdc.202200658"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.202200658","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"value":"1860-7179","type":"print"},{"value":"1860-7187","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,8]]},"assertion":[{"value":"2022-12-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-02-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200658"}}