{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T16:38:35Z","timestamp":1777480715675,"version":"3.51.4"},"reference-count":61,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2022,11,9]],"date-time":"2022-11-09T00:00:00Z","timestamp":1667952000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Deanship of Scientific Research at King Saud University","award":["RGP-163"],"award-info":[{"award-number":["RGP-163"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Human carbonic anhydrase (CA, EC 4.2.1.1) (hCA) isoforms I, II, IX, and XII were investigated for their inhibitory activity with a series of new Schiff\u2019s bases based on quinazoline scaffold 4\u201327. The hCA I isoform was efficiently inhibited by Schiff\u2019s bases 4\u20136, 10\u201319, 22\u201327 and had an inhibition constant (Ki) value of 52.8\u2013991.7 nM compared with AAZ (Ki, 250 nM). Amongst the quinazoline derivatives, the compounds 2, 3, 4, 10, 11, 16, 18, 24, 26, and 27 were proven to be effective hCA II inhibitors, with Ki values of 10.8\u201352.6 nM, measuring up to AAZ (Ki, 12 nM). Compounds 2\u201327 revealed compelling hCA IX inhibitory interest with Ki values of 10.5\u201399.6 nM, rivaling AAZ (Ki, 25.0 nM). Quinazoline derivatives 3, 10, 11, 13, 15\u201319, and 24 possessed potent hCA XII inhibitory activities with KI values of 5.4\u201325.5 nM vs. 5.7 nM of AAZ. Schiff\u2019s bases 7, 8, 9, and 21 represented attractive antitumor hCA IX carbonic anhydrase inhibitors (CAIs) with KI rates (22.0, 34.8, 49.2, and 45.3 nM, respectively). Compounds 5, 7, 8, 9, 14, 18, 19, and 21 showed hCA I inhibitors on hCA IX with a selectivity index of 22.46\u2013107, while derivatives 12, 14, and 18 showed selective hCA I inhibitors on hCA XII with a selectivity profile of 45.04\u201358.58, in contrast to AAZ (SI, 10.0 and 43.86). Compounds 2, 5, 7\u201314, 19\u201323, and 25 showed a selectivity profile for hCA II inhibitors over hCA IX with a selectivity index of 2.02\u201319.67, whereas derivatives 5, 7, 8, 13, 14, 15, 17, 20, 21, and 22 showed selective hCA II inhibitors on hCA XII with a selectivity profile of 4.84\u201326.60 balanced to AAZ (SI, 0.48 and 2.10).<\/jats:p>","DOI":"10.3390\/molecules27227703","type":"journal-article","created":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T02:11:15Z","timestamp":1668046275000},"page":"7703","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Carbonic Anhydrase Inhibition Activities of Schiff\u2019s Bases Based on Quinazoline-Linked Benzenesulfonamide"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7197-1515","authenticated-orcid":false,"given":"Adel S.","family":"El-Azab","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3362-9337","authenticated-orcid":false,"given":"Alaa A.-M.","family":"Abdel-Aziz","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hazem A.","family":"Ghabbour","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Silvia","family":"Bua","sequence":"additional","affiliation":[{"name":"Department of Neurofarba, Sezione di Scienze Farmaceutiche Nutraceutiche, Universit\u00e0 degli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3342-702X","authenticated-orcid":false,"given":"Alessio","family":"Nocentini","sequence":"additional","affiliation":[{"name":"Department of Neurofarba, Sezione di Scienze Farmaceutiche Nutraceutiche, Universit\u00e0 degli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6983-8587","authenticated-orcid":false,"given":"Hamad M.","family":"Alkahtani","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nawaf A.","family":"Alsaif","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9868-0355","authenticated-orcid":false,"given":"Mohamed H. M.","family":"Al-Agamy","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutics and Microbiology, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4262-0323","authenticated-orcid":false,"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"Department of Neurofarba, Sezione di Scienze Farmaceutiche Nutraceutiche, Universit\u00e0 degli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1016\/j.ejmech.2018.06.021","article-title":"Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors","volume":"155","author":"Kumar","year":"2018","journal-title":"Eur. J. Med. 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