{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T18:07:36Z","timestamp":1791828456587,"version":"4.3.4"},"reference-count":49,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2022,5,2]],"date-time":"2022-05-02T00:00:00Z","timestamp":1651449600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2022,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>1\u2010Methyl\/ethyl\/benzyl\u20105\u2010(un)substituted 1<jats:italic>H<\/jats:italic>\u2010indole\u20102,3\u2010diones (<jats:bold>2<\/jats:bold>, <jats:bold>3<\/jats:bold>, and <jats:bold>4<\/jats:bold>) were synthesized by reaction of 5\u2010(un)substituted 1<jats:italic>H<\/jats:italic>\u2010indole\u20102,3\u2010diones (<jats:bold>1<\/jats:bold>) with methyl iodide, ethyl chloride, and benzyl bromide. (3\u2010Sulfamoylphenyl)isothiocyanate (<jats:bold>6<\/jats:bold>) was obtained by the treatment of 3\u2010aminobenzenesulfonamide (<jats:bold>5<\/jats:bold>) with thiophosgene. Compound <jats:bold>6<\/jats:bold> was reacted with hydrazine to yield 4\u2010(3\u2010sulfamoylphenyl)thiosemicarbazide (<jats:bold>7<\/jats:bold>). Novel 1\u2010(un)substituted\/methyl\/ethyl\/benzyl\u20105\u2010(un)substituted 1<jats:italic>H<\/jats:italic>\u2010indole\u20102,3\u2010dione 3\u2010[4\u2010(3\u2010sulfamoylphenyl)thiosemicarbazone] derivatives (<jats:bold>8<\/jats:bold>\u2212<jats:bold>11<\/jats:bold>) were prepared by condensation of <jats:bold>7<\/jats:bold> and <jats:bold>1<\/jats:bold>\u2212<jats:bold>4<\/jats:bold>. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data. Inhibition of the widely distributed cytosolic off\u2010targets human carbonic anhydrases (hCAs) I and II, and two tumor\u2010associated membrane\u2010bound isoforms (hCAs IX and XII), by <jats:bold>8<\/jats:bold>\u2212<jats:bold>11<\/jats:bold> was investigated. The hCA II inhibitory effects of all tested compounds were in the subnanomolar to low nanomolar levels (<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>\u2009=\u20090.32\u221283.3\u2009nM), and generally high selectivity for hCA II isoenzyme over hCA I, IX, and XII isoenzymes was observed. The strongest inhibitors of hCA II, 1\u2010benzyl\u20105\u2010(trifluoromethoxy)\u2010substituted <jats:bold>11c<\/jats:bold> (<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>\u2009=\u20090.32\u2009nM) and 1\u2010ethyl\u20105\u2010chloro\u2010substituted <jats:bold>10e<\/jats:bold> (<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>\u2009=\u20090.35\u2009nM), were docked within the enzyme active site. Molecular modeling studies with the most effective hCA IX and XII inhibitors were also carried out.<\/jats:p>","DOI":"10.1002\/ardp.202200023","type":"journal-article","created":{"date-parts":[[2022,5,2]],"date-time":"2022-05-02T19:25:25Z","timestamp":1651519525000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["New 1<i>H<\/i>\u2010indole\u20102,3\u2010dione 3\u2010thiosemicarbazones with 3\u2010sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors"],"prefix":"10.1002","volume":"355","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8293-2036","authenticated-orcid":false,"given":"P\u0131nar","family":"Eraslan\u2010Elma","sequence":"first","affiliation":[{"name":"Health Sciences Institute Istanbul University  Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8416-0471","authenticated-orcid":false,"given":"Atilla","family":"Akdemir","sequence":"additional","affiliation":[{"name":"Computer\u2010Aided Drug Discovery Laboratory, Department of Pharmacology, Faculty of Pharmacy Bezmialem Vakif University  Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4258-0678","authenticated-orcid":false,"given":"Emanuela","family":"Berrino","sequence":"additional","affiliation":[{"name":"Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences Universit\u00e0 Degli Studi di Firenze  Florence Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5010-0355","authenticated-orcid":false,"given":"Murat","family":"Bozda\u011f","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Science University of Antwerp  Antwerp Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4262-0323","authenticated-orcid":false,"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences Universit\u00e0 Degli Studi di Firenze  Florence Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6916-122X","authenticated-orcid":false,"given":"Nilg\u00fcn","family":"Karal\u0131","sequence":"additional","affiliation":[{"name":"Health Sciences Institute Istanbul University  Istanbul Turkey"},{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Istanbul University  Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,5,2]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.672983"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1113\/jphysiol.1971.sp009458"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.04.020"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.R100045200"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC07320G"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1122001"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2017.1353502"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms17071150"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1152\/physrev.1967.47.4.595"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.2012.649006"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2009.00857.x"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.2013.790957"},{"key":"e_1_2_8_15_1","first-page":"7075","volume":"60","author":"Wykoff C. 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